Supplementary Information

Quantum chemical investigation of thermochemistry in Calvin cycle

DIBYENDU MONDAL, TUMPA SADHUKHAN, IQBAL A LATIF and SAMBHU N DATTA*

Department of Chemistry, Indian Institute of Technology – Bombay, Powai,

Mumbai 400 076, India

e-mail:

*For Correspondence

CONTENTS

Title / Page

Log Files S1. Log files from Gaussian09 Calculation: Optimization and frequency calculation at UM06-2X/6-311++G(3df,3pd) level of theory

/ 2
3-Phosphoglycerate (3-PG) / 2
Adenosine diphosphate (ADP) / 2
Adenosine triphosphate (ATP) / 3
Carbon dioxide (CO2) / 4
Dihydroxyacetone phosphate (DHAP) / 4
Erythose-4-phosphate (E4P) / 5
Fructose-6-phosphate (F6P) / 5
Fructose-1,6- biphosphate (F-1,6-BP) / 6
Glyceraldehyde-3-phosphate (G3P) / 7
Hydroxonium (H3O+) / 7
Phosphate (HPO42-) / 8
Ribose-5-phosphate (R5P) / 8
Ribulose-5-phosphate (Ru5P) / 9
Ribulose-1,5-bisphosphate (RuBP) / 10
Sedoheptulose-7-phosphate (Su7P) / 10
Sedoheptulose-1,7-bisphosphate (Su 1,7BP) / 11
Water (H2O) / 12
Xylulose-5-phosphate (Xu5P) / 12

Log Files S2. Log files from Gaussian09 Calculation: Optimization and frequency calculation at UM06-2X/6-311++G(d,p) level of theory

/ 13
NADP+ / 13
NADPH / 14

Log Files S3. Log files from Gaussian09 Calculation: Optimization and frequency calculation at B3LYP/6-311++G(df,pd) level of theory

/ 15
Phosphate (HPO42-) / 15
Water (H2O) / 16
Full reference [28] of G09 / 17

Log Files S1. Log files from Gaussian09 Calculation: Optimization and frequency calculation at UM06-2X/6-311++G(3df,3pd) level of theory

3-Phosphoglycerate(3-PG)

1\1\GINC-COMPUTE-0-11\Freq\UM062X\6-311++G(3df,3pd)\C3H4O7P1(3-)\SNDAT

TA\23-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM06

2X/6-311++G(3df,3pd) Freq\\3pga opt freq\\-3,1\P,-2.0178090629,-0.0985

986246,0.1192592023\O,-0.3543431705,-0.0250597621,0.2221020708\O,1.914

7434717,1.7985289505,0.1159431224\O,-2.3067543043,-1.1648025016,-0.922

3138918\O,-2.4533994768,1.2925158966,-0.305354278\O,2.4831799438,-1.65

17120897,-0.4996730928\O,-2.41047631,-0.4764218828,1.5319542175\O,2.89

01103171,-0.2926753596,1.2348190141\C,0.3289491061,0.3174607061,-0.954

8439601\C,1.7826916026,0.6200287576,-0.6492445895\C,2.4440124439,-0.55

95472286,0.0937118896\H,-0.1281403035,1.2008308149,-1.4087778225\H,0.2

871240966,-0.5033136154,-1.6752039289\H,2.3028990985,0.7430885672,-1.6

024660744\H,2.3496665479,1.4785213717,0.9231481214\\Version=EM64L-G09R

evA.02\State=1-A\HF=-985.2288082\S2=0.\S2-1=0.\S2A=0.\RMSD=1.340e-09\R

MSF=5.021e-05\ZeroPoint=0.091415\Thermal=0.1018456\Dipole=3.7899849,1.

7739565,-1.6202026\

Zero point energy

Zero-point correction= 0.091415 (Hartree/Particle)

Thermal correction to Energy= 0.101846

Thermal correction to Enthalpy= 0.102790

Thermal correction to Gibbs Free Energy= 0.053700

Sum of electronic and zero-point Energies= -985.137393

Sum of electronic and thermal Energies= -985.126963

Sum of electronic and thermal Enthalpies= -985.126018

Sum of electronic and thermal Free Energies= -985.175108

Adenosine diphosphate (ADP)

1\1\GINC-COMPUTE-0-9\Freq\UM062X\6-311++G(3df,3pd)\C10H12N5O10P2(3-)\S

NDATTA\05-Jun-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk

UM062X/6-311++G(3df,3pd) Freq\\adp opt\\-3,1\P,-3.0237938351,1.0240350

255,1.1797446829\P,-3.8841687992,-0.973425459,-0.8707260954\O,1.365823

6073,1.7243493349,1.1574893234\O,3.0901753168,2.2645496473,-1.92317663

13\O,2.1582137855,4.186479749,-0.3567901932\O,-1.4784995376,1.52710878

15,1.33857415\O,-2.807679138,-0.1610478905,0.1441013244\O,-3.812617971

2,2.1418497559,0.5827426231\O,-3.396169831,0.5128656337,2.5287245284\O

,-3.2145641792,-2.3246903289,-1.0093642048\O,-3.9027773781,-0.16738224

24,-2.1512054713\O,-5.1994277197,-0.9978310048,-0.123296818\N,2.675746

4527,0.004498728,0.2848168562\N,3.7652621967,-1.9197516809,0.643041306

3\N,0.514605291,-0.8886388209,-0.4024677194\N,0.4765840065,-3.28071381

94,-0.347859318\N,2.3103887276,-4.5719379579,0.2344454728\C,2.00594510

7,1.9756831598,-1.0933318656\C,1.1961383511,3.197155488,-0.6714860555\

C,2.4204652159,1.4245626594,0.2787503843\C,0.4677053216,2.675271732,0.

5612229115\C,-0.8535440379,2.0407999099,0.1842077146\C,1.7833129851,-0

.9983960287,-0.0082259043\C,3.8328420367,-0.619346011,0.6720177491\C,2

.4757350731,-2.1758082059,0.2238476111\C,1.7551736038,-3.3645054979,0.

0265244508\C,-0.0731396377,-2.070196204,-0.5357551391\H,1.3643842306,1

.2520508005,-1.591600513\H,0.513016051,3.5415722898,-1.4457306893\H,3.

3477593886,1.9053883174,0.5990654515\H,0.3032483258,3.468512571,1.2892

940557\H,-0.689896314,1.2313031554,-0.528879331\H,-1.4833006734,2.8102

729149,-0.2686821435\H,3.425704398,3.1276534707,-1.651084285\H,1.72475

91591,5.0363874696,-0.2580603058\H,4.694101055,-0.0413079118,0.9628036

481\H,-1.1257601697,-2.06285803,-0.8079142655\H,3.2994553896,-4.641895

5231,0.3924493569\H,1.7979941455,-5.3970179772,-0.021726652\\Version=E

M64L-G09RevA.02\State=1-A\HF=-2097.7197014\S2=0.\S2-1=0.\S2A=0.\RMSD=1

.283e-09\RMSF=1.713e-05\ZeroPoint=0.2733868\Thermal=0.2967676\Dipole=1

9.7809438,3.7842865,-0.0084493\

Zero point energy

Zero-point correction= 0.273387 (Hartree/Particle)

Thermal correction to Energy= 0.296768

Thermal correction to Enthalpy= 0.297712

Thermal correction to Gibbs Free Energy= 0.220961

Sum of electronic and zero-point Energies= -2097.446315

Sum of electronic and thermal Energies= -2097.422934

Sum of electronic and thermal Enthalpies= -2097.421990

Sum of electronic and thermal Free Energies= -2097.498740

Adenosine triphosphate (ATP)

1\1\GINC-COMPUTE-0-1\Freq\UM062X\6-311++G(3df,3pd)\C10H12N5O13P3(4-)\S

NDATTA\17-Nov-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk

UM062X/6-311++G(3df,3pd) Freq\\atp2 opt freq\\-4,1\P,2.5978475248,-1.7

3296762,-1.2322382294\P,4.0326816176,0.1769038634,0.5503428739\P,3.714

0411028,0.312887142,3.5092476861\O,-1.2457678609,-1.0193112219,0.92948

85434\O,-4.3759251746,-2.2112688097,-0.3256330193\O,-2.7599862715,-3.6

424215744,1.2178309765\O,1.3571520481,-1.67173146,-0.1787123413\O,3.76

96405569,-1.2076181111,-0.2895577573\O,2.8799635495,-3.1622554359,-1.5

406245786\O,2.3299604725,-0.8059855241,-2.3635796716\O,3.893147795,-0.

4350343106,2.0056008621\O,2.9533144022,1.1518818719,0.2390783069\O,5.4

476716678,0.5458474727,0.2600322525\O,2.2182564518,0.3471678751,3.7353

121374\O,4.4552144476,-0.6396001916,4.4214338097\O,4.3577131667,1.6739

148442,3.3629486428\N,-2.8667588646,0.5087055778,0.2413233076\N,-3.642

7666527,2.6091621739,0.3158560664\N,-1.6868074354,0.6082239688,-1.8999

137284\N,-1.8668742098,2.773603531,-2.9137170792\N,-3.0502436302,4.524

9142372,-1.965365239\C,-3.0126600476,-1.9144383312,-0.3331343659\C,-2.

1103785567,-3.0602209337,0.1050429511\C,-2.6171737439,-0.8385570399,0.

6873652308\C,-0.8323120991,-2.3251310351,0.4994432248\C,0.1454051551,-

2.2266520239,-0.6476288622\C,-2.4282640249,1.1171075863,-0.910215904\C

,-3.5772835934,1.4610999294,0.9255096074\C,-2.9226514167,2.4096832053,

-0.8416986747\C,-2.6088613909,3.2590809698,-1.9146733915\C,-1.45735216

67,1.5027675287,-2.8489972502\H,-2.7346308008,-1.5811364716,-1.3305021

957\H,-1.9411128815,-3.7915941996,-0.682175319\H,-3.2023937912,-0.9698

429865,1.6010265121\H,-0.3522043383,-2.8204041104,1.3425742944\H,-0.27

7464433,-1.5997596966,-1.4374364218\H,0.3256910744,-3.2311304538,-1.03

76301555\H,-4.539749267,-2.7837512844,0.4331770997\H,-2.2358518852,-4.

3753113432,1.5483203722\H,-4.0243253939,1.2254779044,1.8768643922\H,-0

.8590977553,1.1654989992,-3.6841879838\H,-3.5143100299,4.9176305682,-1

.1660376975\H,-2.7201933172,5.1348649197,-2.6918592841\\Version=EM64L-

G09RevA.02\State=1-A\HF=-2665.0426134\S2=0.\S2-1=0.\S2A=0.\RMSD=1.877e

-09\RMSF=1.865e-05\ZeroPoint=0.2871553\Thermal=0.3153248\Dipole=-23.54

17148,-1.9631241,-7.8388635\

Zero point energy

Zero-point correction= 0.287155 (Hartree/Particle)

Thermal correction to Energy= 0.315325

Thermal correction to Enthalpy= 0.316269

Thermal correction to Gibbs Free Energy= 0.226311

Sum of electronic and zero-point Energies= -2664.755458

Sum of electronic and thermal Energies= -2664.727289

Sum of electronic and thermal Enthalpies= -2664.726344

Sum of electronic and thermal Free Energies= -2664.816303

Carbon dioxide (CO2)

1\1\GINC-LOCALHOST\Freq\UM062X\6-311++G(3df,3pd)\C1O2\SNDATTA\26-May-2

014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM062X/6-311++G

(3df,3pd) Freq\\carbondioxide opt freq\\0,1\C,-1.39999995,-0.37999999,

0.\O,-0.2468833925,-0.37999999,0.\O,-2.5531165075,-0.37999999,0.\\Vers

ion=EM64L-G09RevA.02\State=1-SGG\HF=-188.586875\S2=0.\S2-1=0.\S2A=0.\R

MSD=1.829e-10\RMSF=7.066e-05\ZeroPoint=0.0118708\Thermal=0.0144772\Dip

ole=0.,0.,0.\

Zero point energy

Zero-point correction= 0.011871 (Hartree/Particle)

Thermal correction to Energy= 0.014477

Thermal correction to Enthalpy= 0.015421

Thermal correction to Gibbs Free Energy= -0.008805

Sum of electronic and zero-point Energies= -188.575004

Sum of electronic and thermal Energies= -188.572398

Sum of electronic and thermal Enthalpies= -188.571454

Sum of electronic and thermal Free Energies= -188.595680

Dihydroxyacetone phosphate (DHAP)

1\1\GINC-COMPUTE-0-12\Freq\UM062X\6-311++G(3df,3pd)\C3H5O6P1(2-)\SNDAT

TA\23-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM06

2X/6-311++G(3df,3pd) Freq\\dhap opt freq\\-2,1\P,-2.2224651249,-0.0639

426294,-0.0167222337\O,-0.6444650636,0.5188938553,0.0927619038\O,4.093

1415084,-0.2308474882,0.0980860981\O,1.9631080683,1.3015739796,0.13097

87157\O,-3.0303674117,1.2031353697,0.1208091395\O,-2.343792487,-1.0350

276878,1.1406160629\O,-2.2811579782,-0.7297172148,-1.3771651709\C,0.33

40471064,-0.4541321444,0.0026007621\C,1.7155414235,0.1201800573,0.0980

169382\C,2.8538676005,-0.878568756,0.1520441773\H,0.2272070784,-1.2157

250346,0.7854325721\H,0.2806131277,-0.9918851514,-0.9534101159\H,2.750

6547006,-1.5803770848,-0.6768673728\H,2.7478498639,-1.4496087622,1.078

1875393\H,3.9004175875,0.7146486916,0.1586309845\\Version=EM64L-G09Rev

A.02\State=1-A\HF=-910.4324654\S2=0.\S2-1=0.\S2A=0.\RMSD=3.386e-09\RMS

F=1.534e-05\ZeroPoint=0.0981332\Thermal=0.1084909\Dipole=7.579139,-1.1

144964,0.2277444\

Zero point energy

Zero-point correction= 0.098133 (Hartree/Particle)

Thermal correction to Energy= 0.108491

Thermal correction to Enthalpy= 0.109435

Thermal correction to Gibbs Free Energy= 0.060693

Sum of electronic and zero-point Energies= -910.334332

Sum of electronic and thermal Energies= -910.323975

Sum of electronic and thermal Enthalpies= -910.323030

Sum of electronic and thermal Free Energies= -910.371773

Erythose-4-phosphate (E4P)

1\1\GINC-COMPUTE-0-10\Freq\UM062X\6-311++G(3df,3pd)\C4H7O7P1(2-)\SNDAT

TA\24-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM06

2X/6-311++G(3df,3pd) Freq\\e4p opt freq\\-2,1\P,-2.3135545772,0.511879

905,-0.1301793894\O,-1.057218109,-0.3779733685,0.5402127857\O,1.981319

0857,-1.7330460179,-0.7739661427\O,3.0351106291,-0.1240408341,1.127078

8566\O,2.4426033068,1.8159161522,-0.5344706151\O,-2.9893791528,1.07519

22716,1.0976113241\O,-3.1276103759,-0.4970179797,-0.912529217\O,-1.615

9312981,1.5434019131,-0.9995708241\C,1.1246924952,-1.2662431466,0.2441

29859\C,1.6731703782,0.0473141902,0.826499791\C,-0.2529777501,-1.08272

02863,-0.3642391826\C,1.4841902209,1.2051489194,-0.1222017695\H,1.0851

523559,-1.9885979901,1.0638109324\H,1.0997207806,0.2819382161,1.726160

6925\H,-0.6866974245,-2.0547616274,-0.6056151547\H,-0.1388846897,-0.52

89559732,-1.3019501859\H,0.449079837,1.4656701354,-0.3973277733\H,2.87

55098091,-1.7004220945,-0.4173675056\H,3.5076044788,0.5748176152,0.653

9135185\\Version=EM64L-G09RevA.02\State=1-A\HF=-1024.9636674\S2=0.\S2-

1=0.\S2A=0.\RMSD=8.474e-10\RMSF=3.692e-05\ZeroPoint=0.1332066\Thermal=

0.1451898\Dipole=7.6213803,-2.1193408,1.0991371\

Zero point energy

Zero-point correction= 0.133207 (Hartree/Particle)

Thermal correction to Energy= 0.145190

Thermal correction to Enthalpy= 0.146134

Thermal correction to Gibbs Free Energy= 0.094407

Sum of electronic and zero-point Energies= -1024.830461

Sum of electronic and thermal Energies= -1024.818478

Sum of electronic and thermal Enthalpies= -1024.817533

Sum of electronic and thermal Free Energies= -1024.869261

Fructose-6-phosphate (F6P)

1\1\GINC-COMPUTE-0-9\Freq\UM062X\6-311++G(3df,3pd)\C6H11O9P1(2-)\SNDAT

TA\29-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM06

2X/6-311++G(3df,3pd) Freq\\f6p opt freq\\-2,1\P,-4.1497802736,-0.40897

57132,0.2114090823\O,1.148027693,-0.5031173144,-1.4522147812\O,-0.4000

57833,0.9745395951,1.4783049291\O,-2.6877507527,0.4259045482,0.2212281

165\O,2.1123882544,1.960250739,-0.3411370039\O,4.3307993987,0.57330384

57,-0.5885112412\O,4.9383144459,-1.8472370545,0.2806280745\O,-3.942849

7634,-1.5603917263,1.1741576122\O,-4.3288074003,-0.8391055188,-1.23000

78946\O,-5.1104394371,0.6554833092,0.6874483686\C,0.9603131458,-0.1504

106299,-0.0971073767\C,-0.3501353576,0.5894600052,0.1190685398\C,2.144

1638514,0.7210386169,0.3071073408\C,-1.552754477,-0.2804103084,-0.1986

122812\C,3.4459783869,0.009585364,0.0110994078\C,3.624607915,-1.412221

4335,0.474278161\H,0.9624118984,-1.039037545,0.5426432746\H,-0.3587882

616,1.4721025803,-0.5245663033\H,2.0882476626,0.8563677151,1.391881543

2\H,-1.6006912677,-0.4956409179,-1.2694642807\H,-1.4723701417,-1.22574

72609,0.3497844249\H,0.497265867,-1.1635918248,-1.7016033516\H,-1.3383

528291,1.0977195564,1.6688781363\H,3.3459600012,-1.4826196064,1.526951

6513\H,2.9152932972,-2.0200049983,-0.0962791989\H,2.9689357691,2.07613

02291,-0.7711019282\H,5.3816702081,-1.1686742517,-0.2437630214\\Versio

n=EM64L-G09RevA.02\State=1-A\HF=-1254.0344973\S2=0.\S2-1=0.\S2A=0.\RMS

D=3.359e-09\RMSF=2.147e-05\ZeroPoint=0.2002235\Thermal=0.2172577\Dipol

e=13.6229568,0.3252405,-0.3851142\

Zero point energy

Zero-point correction= 0.200224 (Hartree/Particle)

Thermal correction to Energy= 0.217258

Thermal correction to Enthalpy= 0.218202

Thermal correction to Gibbs Free Energy= 0.154698

Sum of electronic and zero-point Energies= -1253.834274

Sum of electronic and thermal Energies= -1253.817240

Sum of electronic and thermal Enthalpies= -1253.816295

Sum of electronic and thermal Free Energies= -1253.879800

Fructose-1,6- biphosphate (F-1,6-BP)

1\1\GINC-COMPUTE-0-10\Freq\UM062X\6-311++G(3df,3pd)\C6H10O12P2(4-)\SND

ATTA\06-Jun-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM

062X/6-311++G(3df,3pd) Freq\\f16bp opt freq\\-4,1\P,5.1436812785,-0.87

43504789,0.0360440645\O,-0.0535332572,0.3190262662,1.4346166505\O,1.86

48436357,1.350638919,-1.4675784037\O,3.9169180236,0.2632731046,-0.1424

033447\O,-0.3607357193,2.9548393341,0.3891663465\O,-2.8391369641,2.189

1041127,0.5429643075\O,-4.0040053679,0.0552796022,-0.7871319275\O,4.69

85872845,-2.0541056817,-0.8044189027\O,5.1869600105,-1.1593237649,1.52

31144452\O,6.3356846257,-0.1199783405,-0.5051670441\C,0.2324444457,0.6

328047198,0.0867418176\C,1.6917249624,1.0137310775,-0.1046297749\C,-0.

6801178657,1.7862512674,-0.3131016578\C,2.6294201907,-0.1237037171,0.2

553010344\C,-2.1437831597,1.4300003605,-0.0874434037\C,-2.6279193292,0

.1364726927,-0.6863775613\H,0.014548779,-0.2176917234,-0.5666446458\H,

1.9089771057,1.8783410956,0.5273510684\H,-0.5455432248,1.9425250794,-1

.3877080945\H,2.5979266984,-0.3228303836,1.3306478417\H,2.3253656131,-

1.0301910133,-0.2799155373\H,0.4043513527,-0.4893572741,1.6768341847\H

,2.8082851146,1.2402474749,-1.6358914668\H,-2.1561425786,0.0367130915,

-1.6710483684\H,-2.2190638198,-0.6695167968,-0.0638490292\H,-1.1783725

783,3.2316523996,0.8255313157\P,-4.8552743356,-1.1699665532,0.00658788

87\O,-3.8195006441,-2.2514892733,0.2358598145\O,-5.9313419793,-1.51576

47919,-0.9979016013\O,-5.3793681096,-0.5319317122,1.2761454067\\Versio

n=EM64L-G09RevA.02\State=1-A\HF=-1820.8811589\S2=0.\S2-1=0.\S2A=0.\RMS

D=5.203e-09\RMSF=2.441e-05\ZeroPoint=0.2027149\Thermal=0.2229821\Dipol

e=0.0037459,6.337287,-1.0254844\

Zero point energy

Zero-point correction= 0.202715 (Hartree/Particle)

Thermal correction to Energy= 0.222982

Thermal correction to Enthalpy= 0.223926

Thermal correction to Gibbs Free Energy= 0.152184

Sum of electronic and zero-point Energies= -1820.678444

Sum of electronic and thermal Energies= -1820.658177

Sum of electronic and thermal Enthalpies= -1820.657233

Sum of electronic and thermal Free Energies= -1820.728975

Glyceraldehyde-3-phosphate (G3P)

1\1\GINC-COMPUTE-0-12\Freq\UM062X\6-311++G(3df,3pd)\C3H5O6P1(2-)\SNDAT

TA\23-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM06

2X/6-311++G(3df,3pd) Freq\\ga3p opt freq\\-2,1\P,1.8228199957,-0.09378

71166,-0.0865712879\O,0.144618349,-0.1642612184,-0.1334145203\O,-2.371

6083454,1.1876783255,-0.8163573461\O,2.2104429868,-1.1937331032,-1.047

0507089\O,2.1754109009,-0.3557569464,1.3644172521\O,2.1563609624,1.309

5541231,-0.5514883794\O,-2.9870474368,-1.3476082051,-0.3822338249\C,-0

.5196286176,0.7453664893,0.6952745116\C,-2.0141244873,0.6570911371,0.4

29643689\C,-2.4196249835,-0.7878344585,0.5192187839\H,-0.3325468945,0.

5184097262,1.7491668942\H,-0.1870772761,1.7674712423,0.5003132983\H,-2

.5341889302,1.1917008651,1.2315467168\H,-2.1580382937,-1.30728975,1.45

14627083\H,-2.7753843128,0.4691506803,-1.3197925325\\Version=EM64L-G09

RevA.02\State=1-A\HF=-910.4264298\S2=0.\S2-1=0.\S2A=0.\RMSD=2.448e-09\

RMSF=2.221e-05\ZeroPoint=0.0989382\Thermal=0.108863\Dipole=-7.1962892,

0.6370236,1.7979223\

Zero point energy

Zero-point correction= 0.098938 (Hartree/Particle)

Thermal correction to Energy= 0.108863

Thermal correction to Enthalpy= 0.109807

Thermal correction to Gibbs Free Energy= 0.062597

Sum of electronic and zero-point Energies= -910.327492

Sum of electronic and thermal Energies= -910.317567

Sum of electronic and thermal Enthalpies= -910.316623

Sum of electronic and thermal Free Energies= -910.363833

Hydroxonium (H3O+)

1\1\GINC-LOCALHOST\Freq\UM062X\6-311++G(3df,3pd)\H3O1(1+)\SNDATTA\26-M

ay-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM062X/6-31

1++G(3df,3pd) Freq\\hydroxonium opt freq\\1,1\O,0.27926929,1.716918470

9,-1.36952478\H,1.242499259,1.6284100755,-1.36952478\H,-0.1256951756,2

.5953542914,-1.36952478\H,-0.2789962133,0.9269910458,-1.36952478\\Vers

ion=EM64L-G09RevA.02\State=1-A1'\HF=-76.8147561\S2=0.\S2-1=0.\S2A=0.\R

MSD=1.526e-07\RMSF=1.725e-04\ZeroPoint=0.0332105\Thermal=0.0360499\Dip

ole=0.,0.,0.\

Zero point energy

Zero-point correction= 0.033210 (Hartree/Particle)

Thermal correction to Energy= 0.036050

Thermal correction to Enthalpy= 0.036994

Thermal correction to Gibbs Free Energy= 0.015829

Sum of electronic and zero-point Energies= -76.781546

Sum of electronic and thermal Energies= -76.778706

Sum of electronic and thermal Enthalpies= -76.777762

Sum of electronic and thermal Free Energies= -76.798927

Phosphate (HPO42-)

1\1\GINC-LOCALHOST\Freq\UM062X\6-311++G(3df,3pd)\H1O4P1(2-)\SNDATTA\27

-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM062X/6-

311++G(3df,3pd) Freq\\phosphate opt freq\\-2,1\P,-0.1309693828,-0.5602

055525,-0.1042851784\O,0.4381068125,0.2352421146,-1.2643549327\O,0.438

087507,-1.9625860028,0.0045716668\O,-1.6363026629,-0.4793543953,0.0357

300354\O,0.3876758121,0.2353035042,1.2735746296\H,1.3467441341,0.24341

15402,1.2876685938\\Version=EM64L-G09RevA.02\State=1-A\HF=-643.280545\

S2=0.\S2-1=0.\S2A=0.\RMSD=3.981e-06\RMSF=1.206e-04\ZeroPoint=0.0259269

\Thermal=0.0309522\Dipole=1.2135669,0.6836858,1.1842151\

Zero point energy

Zero-point correction= 0.025927 (Hartree/Particle)

Thermal correction to Energy= 0.030952

Thermal correction to Enthalpy= 0.031896

Thermal correction to Gibbs Free Energy= -0.002575

Sum of electronic and zero-point Energies= -643.254618

Sum of electronic and thermal Energies= -643.249593

Sum of electronic and thermal Enthalpies= -643.248649

Sum of electronic and thermal Free Energies= -643.283120

Ribose-5-phosphate (R5P)

1\1\GINC-COMPUTE-0-11\Freq\UM062X\6-311++G(3df,3pd)\C5H9O8P1(2-)\SNDAT

TA\25-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM06

2X/6-311++G(3df,3pd) Freq\\r5p opt freq\\-2,1\P,-3.3365771123,0.148571

3798,0.1503978106\O,0.4796699322,1.8323642341,0.4971166033\O,1.5209036

383,-1.26314692,-1.0051912429\O,-1.6673072127,0.2789723956,0.320695152

2\O,3.194692662,-1.259852436,1.1353696292\O,4.5005216837,0.4906197858,

-0.3371433458\O,-3.5291456907,-1.0474246791,-0.7592180838\O,-3.7665918

691,1.4641371183,-0.4660246328\O,-3.7782656107,-0.0566010392,1.5808572

969\C,1.2195949914,-0.4274130801,0.0882039541\C,0.4907586477,0.7944897

761,-0.4623403997\C,2.5171341971,-0.0698958279,0.8274600286\C,-0.93435

77258,0.4582333934,-0.8638848609\C,3.3940254171,0.8278862364,-0.004571

3688\H,1.0384873195,1.1460179905,-1.3381345111\H,0.5709044647,-0.94285

51744,0.8016235786\H,2.2588649499,0.4856929321,1.7320306624\H,-0.94747

04926,-0.4433642307,-1.4779491515\H,-1.3544953539,1.2860798398,-1.4394

336708\H,-0.3187181614,1.6766722412,1.0193239981\H,2.0808905509,-1.970

8978756,-0.6684416778\H,2.9796047977,1.8072403733,-0.275707441\H,4.083

375977,-1.1818264333,0.7621616728\\Version=EM64L-G09RevA.02\State=1-A\

HF=-1139.4956509\S2=0.\S2-1=0.\S2A=0.\RMSD=1.242e-09\RMSF=2.769e-05\Ze

roPoint=0.1665806\Thermal=0.1810138\Dipole=11.3148093,0.3043375,-0.144

0823\

Zero point energy

Zero-point correction= 0.166581 (Hartree/Particle)

Thermal correction to Energy= 0.181014

Thermal correction to Enthalpy= 0.181958

Thermal correction to Gibbs Free Energy= 0.124128

Sum of electronic and zero-point Energies= -1139.329070

Sum of electronic and thermal Energies= -1139.314637

Sum of electronic and thermal Enthalpies= -1139.313693

Sum of electronic and thermal Free Energies= -1139.371523

Ribulose-5-phosphate (Ru5P)

1\1\GINC-COMPUTE-0-10\Freq\UM062X\6-311++G(3df,3pd)\C5H9O8P1(2-)\SNDAT

TA\27-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM06

2X/6-311++G(3df,3pd) Freq\\ru5p opt freq\\-2,1\P,-3.0187802347,-0.3564

588449,0.2125754721\O,-1.6790076934,0.1036848049,-0.70110752\O,-0.0894

759412,2.2103206353,-1.1139273331\O,1.6282655244,1.8994028187,1.100464

1297\O,2.9385740518,-0.3583479309,1.2588167152\O,3.6987285682,-2.04940

94309,-0.6150064865\O,-3.0884610308,0.674076066,1.3199215272\O,-2.6815

007336,-1.7525605389,0.6938279219\O,-4.1275225226,-0.2800968401,-0.809

0227578\C,0.5050342442,0.9633510329,-0.8381625967\C,1.8224006829,1.218

9198795,-0.1050459141\C,-0.4488695311,0.1015004054,-0.029971355\C,2.56

72091502,-0.0769565273,0.143843077\C,2.853155709,-1.008519669,-1.00513

99519\H,0.7412075327,0.4551014056,-1.7799225524\H,2.4514787813,1.81887

03298,-0.7712252211\H,-0.0517445448,-0.9150846338,0.0638344411\H,-0.56

11462246,0.5271210407,0.9699905344\H,1.892512423,-1.3956508973,-1.3608

487814\H,3.2947703041,-0.4349985398,-1.8222080302\H,-1.0320125603,2.02

04527792,-1.2060045141\H,2.0266743508,1.3629482309,1.797596055\H,3.804

2096944,-1.9847655759,0.342723141\\Version=EM64L-G09RevA.02\State=1-A\

HF=-1139.4995366\S2=0.\S2-1=0.\S2A=0.\RMSD=3.067e-09\RMSF=9.505e-06\Ze

roPoint=0.1671928\Thermal=0.1815645\Dipole=10.8888413,1.1254326,-1.748

8158\

Zero point energy

Zero-point correction= 0.167193 (Hartree/Particle)

Thermal correction to Energy= 0.181565

Thermal correction to Enthalpy= 0.182509

Thermal correction to Gibbs Free Energy= 0.124900

Sum of electronic and zero-point Energies= -1139.332344

Sum of electronic and thermal Energies= -1139.317972

Sum of electronic and thermal Enthalpies= -1139.317028

Sum of electronic and thermal Free Energies= -1139.374637

Ribulose-1,5-bisphosphate (RuBP)

1\1\GINC-COMPUTE-0-10\Freq\UM062X\6-311++G(3df,3pd)\C5H8O11P2(4-)\SNDA

TTA\30-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM0

62X/6-311++G(3df,3pd) Freq\\rubp opt freq\\-4,1\P,-3.8483746845,-1.253

5397079,0.1291839334\P,4.0659632264,-0.9769416415,-0.2554386656\O,-1.8

825237263,1.9213305189,-1.7105961724\O,-0.7607452788,3.0023217878,0.64

21448164\O,-2.6449023159,-0.4447493811,-0.7237868955\O,3.050041671,0.1

373952871,0.4979310195\O,1.2277901053,1.7229180009,1.7070592255\O,-4.6

278912073,-1.9029385635,-0.9908819931\O,-4.5879893749,-0.1628988974,0.

8763565592\O,-3.0999473208,-2.2141415936,1.030273605\O,5.1580576574,-1

.1291545531,0.7748857384\O,4.485792619,-0.2972638369,-1.5430862927\O,3

.1938291666,-2.1972323094,-0.4650613965\C,-0.9634814837,1.180132354,-0

.9369484809\C,-0.0453771589,2.1694425894,-0.2257327658\C,-1.7107976742

,0.2802553246,0.0303514307\C,1.0655005167,1.4583212654,0.5405266315\C,

1.9137514303,0.4735924192,-0.2136069081\H,-0.3467013406,0.5599856073,-

1.5957471316\H,0.4470970047,2.7686102168,-0.9998923983\H,-1.0077272286

,-0.3883308105,0.5386500788\H,-2.2171727314,0.895503224,0.7777666187\H

,1.2832961327,-0.4071331413,-0.4068910664\H,2.1522498617,0.9037650148,

-1.1939026917\H,-2.6225204937,1.3216683431,-1.8659756497\H,-0.29951737

23,2.9600824831,1.4911188511\\Version=EM64L-G09RevA.02\State=1-A\HF=-1

706.350005\S2=0.\S2-1=0.\S2A=0.\RMSD=5.005e-09\RMSF=1.559e-05\ZeroPoin

t=0.1689372\Thermal=0.1868847\Dipole=-0.4013922,7.611775,-0.8649527\

Zero point energy

Zero-point correction= 0.168937 (Hartree/Particle)

Thermal correction to Energy= 0.186885

Thermal correction to Enthalpy= 0.187829

Thermal correction to Gibbs Free Energy= 0.121344

Sum of electronic and zero-point Energies= -1706.181068

Sum of electronic and thermal Energies= -1706.163120

Sum of electronic and thermal Enthalpies= -1706.162176

Sum of electronic and thermal Free Energies= -1706.228661

Sedoheptulose-7-phosphate (Su7P)

1\1\GINC-COMPUTE-0-11\Freq\UM062X\6-311++G(3df,3pd)\C7H13O10P1(2-)\SND

ATTA\30-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM

062X/6-311++G(3df,3pd) Freq\\su7p opt\\-2,1\P,4.036565549,-1.073433539

4,-0.0308621964\O,-0.3569151174,1.8505683803,-1.507369682\O,-1.2503331

195,-0.0434955235,1.4435932486\O,1.7834752456,2.6165873258,-0.01539671

82\O,-3.178367998,1.7970302855,0.3553448971\O,3.0509106901,0.176441279

6,0.4947947541\O,-4.5726222572,-0.3845581652,0.6572631603\O,-4.1451546

642,-2.8110363227,-0.3454817531\O,5.2794742075,-0.864708002,0.80390900

57\O,4.2163007937,-0.829470153,-1.5167204824\O,3.2588184321,-2.3367904

468,0.2847544887\C,-0.3713086756,1.6081712477,-0.1155697528\C,-1.23801

66044,0.3745585867,0.0956318462\C,1.0580992579,1.4728498778,0.41798710

6\C,-2.6838509066,0.6647349933,-0.2998934201\C,1.7857722299,0.24790692

23,-0.0940927403\C,-3.567909428,-0.5348032438,0.0110646747\C,-3.129865

7949,-1.8667810341,-0.5312205794\H,-0.8385304197,2.4463375158,0.409456

3814\H,-0.8652567081,-0.4152245188,-0.5629229547\H,1.0339850165,1.4394

03346,1.5086614288\H,-2.6959213422,0.8167009524,-1.3833698774\H,1.8669

858421,0.3043006361,-1.1835206635\H,1.2107692799,-0.6541023623,0.15038

35838\H,0.3787440892,2.4510332655,-1.673536429\H,-0.3975219903,-0.4241

581306,1.6707569352\H,1.4951249322,3.3792098264,0.4923664741\H,-3.9903

511802,1.5245080991,0.8029102931\H,-2.2126502786,-2.1357909942,0.00170

25779\H,-2.8706940407,-1.7312077826,-1.585148548\H,-3.8156550398,-3.66

75823215,-0.6250750583\\Version=EM64L-G09RevA.02\State=1-A\HF=-1368.55

9149\S2=0.\S2-1=0.\S2A=0.\RMSD=5.379e-10\RMSF=2.925e-05\ZeroPoint=0.23

35875\Thermal=0.2529118\Dipole=-13.0261157,3.5253299,-0.2483866\

Zero point energy

Zero-point correction= 0.233588

(Hartree/Particle)

Thermal correction to Energy= 0.252912

Thermal correction to Enthalpy= 0.253856

Thermal correction to Gibbs Free Energy= 0.185108

Sum of electronic and zero-point Energies= -1368.325561

Sum of electronic and thermal Energies= -1368.306237

Sum of electronic and thermal Enthalpies= -1368.305293

Sum of electronic and thermal Free Energies= -1368.374041

Sedoheptulose-1,7-bisphosphate (Su 1,7BP)

1\1\GINC-COMPUTE-0-6\Freq\UM062X\6-311++G(3df,3pd)\C7H12O13P2(4-)\SNDA

TTA\01-Jun-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM0

62X/6-311++G(3df,3pd) Freq\\su17bp opt\\-4,1\P,4.3132797991,-2.0325129

316,0.1613765661\P,-4.3559143576,-2.0331866818,-0.2121978059\O,1.26122

51408,2.1363702679,-1.7080499687\O,-0.043368406,1.1202706258,1.5126229

982\O,3.6319510602,2.2707775693,-0.3140068525\O,-1.2071578725,3.420994

7995,0.2136043267\O,3.9450824705,-0.4214106907,0.4375316161\O,-3.24288

36297,2.0330859976,0.9845757219\O,-3.948734354,-0.481017683,0.30183569

61\O,5.608494474,-2.1921348727,0.926411756\O,4.4431803294,-2.152477819

8,-1.3447469457\O,3.1376571056,-2.7997328316,0.7350399332\O,-5.6819903

807,-2.2437137645,0.4783600528\O,-3.2212646346,-2.9036426484,0.2877906

422\O,-4.4250556788,-1.9253864553,-1.7217406915\C,1.2564302423,2.09762

47243,-0.29525346\C,0.0069859256,1.329180537,0.1159230299\C,2.56409824

74,1.5024114255,0.2285462195\C,-1.2495832081,2.1080043544,-0.270252286

3\C,2.7872351153,0.0616782752,-0.1789849085\C,-2.4947937765,1.41025016

63,0.2712335259\C,-2.7191360846,-0.018885907,-0.1302877362\H,1.1789883

988,3.1109073465,0.109388855\H,-0.0090122809,0.3793325212,-0.425762858

6\H,2.5742778436,1.5675592691,1.318309577\H,-1.3085204008,2.1103493125

,-1.3608038277\H,2.872959201,0.0035468991,-1.2679765902\H,1.9230658214

,-0.5445217821,0.1171777791\H,2.142418122,2.4240383827,-1.9710682185\H

,0.6081930048,0.4584755297,1.7588479749\H,3.659174534,3.1197356743,0.1

338726339\H,-1.892555334,-0.6077104949,0.289402229\H,-2.6191533607,-0.

0785957702,-1.2218657146\H,-1.9867730764,3.5192366555,0.7780467317\\Ve

rsion=EM64L-G09RevA.02\State=1-A\HF=-1935.4126976\S2=0.\S2-1=0.\S2A=0.

\RMSD=5.301e-09\RMSF=1.056e-05\ZeroPoint=0.2369739\Thermal=0.2594597\D

ipole=1.511647,14.4721997,0.1355933\

Zero point energy

Zero-point correction= 0.236974 (Hartree/Particle)

Thermal correction to Energy= 0.259460

Thermal correction to Enthalpy= 0.260404

Thermal correction to Gibbs Free Energy= 0.184107

Sum of electronic and zero-point Energies= -1935.175724

Sum of electronic and thermal Energies= -1935.153238

Sum of electronic and thermal Enthalpies= -1935.152294

Sum of electronic and thermal Free Energies= -1935.228590

Water (H2O)

1\1\GINC-LOCALHOST\Freq\UM062X\6-311++G(3df,3pd)\H2O1\SNDATTA\26-May-2

014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM062X/6-311++G

(3df,3pd) Freq\\water opt freq\\0,1\O,-0.8720410305,1.0029622772,0.\H,

0.0864787475,1.0423296195,0.\H,-1.1548921991,1.9196438844,0.\\Version=

EM64L-G09RevA.02\State=1-A1\HF=-76.4295817\S2=0.\S2-1=0.\S2A=0.\RMSD=2

.612e-06\RMSF=1.314e-05\ZeroPoint=0.0214804\Thermal=0.0243163\Dipole=0

.501591,0.7097348,0.\

Zero point energy

Zero-point correction= 0.021480 (Hartree/Particle)

Thermal correction to Energy= 0.024316

Thermal correction to Enthalpy= 0.025260

Thermal correction to Gibbs Free Energy= 0.003845

Sum of electronic and zero-point Energies= -76.408101

Sum of electronic and thermal Energies= -76.405265

Sum of electronic and thermal Enthalpies= -76.404321

Sum of electronic and thermal Free Energies= -76.425737

Xylulose-5-phosphate (Xu5P)

1\1\GINC-COMPUTE-0-10\Freq\UM062X\6-311++G(3df,3pd)\C5H9O8P1(2-)\SNDAT

TA\27-May-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM06

2X/6-311++G(3df,3pd) Freq\\rubp opt freq\\-2,1\P,-3.5028414401,-0.1309

919499,-0.0232995267\O,0.4759499908,-0.2670213059,-1.347167407\O,-1.89

11737917,-0.6081950764,-0.1308199262\O,1.3348435011,1.9951250356,0.093

130536\O,3.6448952638,0.8149314822,-0.5967441686\O,4.5363898945,-1.586

2329688,0.0002260626\O,-4.2111396947,-1.2819580697,-0.6981517949\O,-3.

5643494568,1.1840893874,-0.7723255726\O,-3.755301344,-0.0008203752,1.4

646509805\C,0.4129748378,-0.2479599404,0.0664508088\C,1.5338291762,0.6

805882973,0.5220643329\C,-0.9580529139,0.2183472108,0.5136994328\C,2.8

686084043,0.1392402148,0.0298803908\C,3.2069082078,-1.3045366448,0.328

2278589\H,0.5903735283,-1.2507756611,0.4665594207\H,1.5645797784,0.684

7458301,1.6123673597\H,-1.0457794462,0.1436066553,1.6000183854\H,-1.10

28551646,1.2601070501,0.2194768542\H,3.0182992177,-1.5127711527,1.3831

362625\H,2.5179925378,-1.9210501809,-0.2573858431\H,-0.4036328465,-0.5

357209929,-1.6406602014\H,1.2095073833,1.9634606826,-0.8619998688\H,4.

8638743767,-0.8215075278,-0.4912343765\\Version=EM64L-G09RevA.02\State

=1-A\HF=-1139.5006578\S2=0.\S2-1=0.\S2A=0.\RMSD=3.584e-09\RMSF=2.381e-

05\ZeroPoint=0.1660221\Thermal=0.1808355\Dipole=11.0749679,-0.4092285,

0.6582609\

Zero point energy

Zero-point correction= 0.166022 (Hartree/Particle)

Thermal correction to Energy= 0.180835

Thermal correction to Enthalpy= 0.181780

Thermal correction to Gibbs Free Energy= 0.122956

Sum of electronic and zero-point Energies= -1139.334636

Sum of electronic and thermal Energies= -1139.319822

Sum of electronic and thermal Enthalpies= -1139.318878

Sum of electronic and thermal Free Energies= -1139.377701

Log Files S2. Log files from Gaussian09 Calculation: Optimization and frequency calculation at UM06-2X/6-311++G(d,p) level of theory

NADP+

1\1\GINC-COMPUTE-0-3\Freq\UM062X\6-311++G(d,p)\C21H25N7O17P3(3-)\SNDAT

TA\10-Dec-2014\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UM06

2X/6-311++G(d,p) Freq\\opt freq\\-3,1\P,-2.4567403196,3.3257846932,-2.

9939155675\P,2.5152953741,3.139952387,2.5190436741\P,4.7747807721,1.27

90008545,1.8951337571\O,-0.0144875308,0.1925912328,0.0161635393\O,3.16

74441433,-2.6865807642,-0.7495791101\O,-1.7197553558,1.8161739671,-2.6

350140036\O,1.0291667586,1.7595207584,-2.3095129215\O,4.1657741708,-1.

077637233,-3.1364308298\O,1.4091487844,-0.8565368271,-3.2336950981\O,1

.217598864,3.2756254084,1.5332695965\O,4.735016812,0.2931967584,0.5847

343604\O,3.3280120943,2.0084484241,1.6429305749\O,-2.9118675045,3.1051

961641,-4.4292053861\O,-1.3289737467,4.3379092858,-2.8056594932\O,-3.5

770422617,3.4426933128,-1.9624788976\O,3.2292001183,4.4490767045,2.469

5791871\O,2.0986104744,2.5371650689,3.822810872\O,5.8898348447,2.24155

79751,1.6627767827\O,4.7066395144,0.4447831716,3.1340939284\O,-1.95696

13596,-3.441954373,2.540179941\N,-2.2081660821,-0.4063065836,-0.526544

6002\N,0.9039493892,-3.1040829976,-1.1750336873\N,-3.8164807473,-1.966

5869304,-0.4018917701\N,-2.5777740588,0.7154024024,1.6167770919\N,-4.2

90690585,-0.3736445863,2.9036814209\N,-5.4906872402,-2.2018937268,2.13

73576619\N,-0.6692694704,-1.5715445732,2.400690417\C,-1.1692139901,1.7

060565408,-1.3710924446\C,0.264950496,2.206482551,-1.1904779939\C,-1.0

055507125,0.2343852765,-1.0042606921\C,0.6952457235,1.4590520882,0.066

881577\C,3.5408717805,-0.668522882,-1.9424019987\C,2.0749460619,-1.081

785908,-2.0321597196\C,3.9973568646,-1.4990744249,-0.7404493951\C,2.18

35026667,-2.5715069752,-1.7259243008\C,0.3568386519,2.1566542044,1.374

3261566\C,3.8322164181,-0.7943555814,0.5938435185\C,-2.8465818676,-0.1

988982695,0.6768153884\C,-2.8477232718,-1.4678946119,-1.1194069491\C,-

3.8174751156,-1.1892708104,0.7392172069\C,0.5182825838,-2.7234374755,0

.0573280155\C,0.1397832749,-3.9068149977,-1.9373645333\C,-0.6853439752

,-3.1541938774,0.5731112718\C,-4.5555942259,-1.2629927151,1.9371757399

\C,-1.0630954561,-4.3836844997,-1.4587276719\C,-1.4743705477,-4.016392

7151,-0.1862645828\C,-3.3458597294,0.5506033056,2.6866351191\C,-1.1727

278311,-2.7327845965,1.9368424576\H,-1.8017591242,2.1869048265,-0.6127

865177\H,0.3157719865,3.2886719977,-1.0896642029\H,-0.6786879387,-0.33

76337471,-1.8816060996\H,1.7696493912,1.2551922983,0.0374988125\H,3.65

32744254,0.4028061132,-1.7559848843\H,1.5472119315,-0.6156122812,-1.19

65206851\H,5.0340495942,-1.8133469941,-0.8610074292\H,2.4032681741,-3.

1624887945,-2.6164663429\H,0.4691901133,1.4515171137,2.2043112947\H,-0

.6752041064,2.5049893854,1.3717115593\H,4.0595422627,-1.4818695646,1.4

101863085\H,2.8008373719,-0.4356167546,0.7261736672\H,1.8632269079,2.2

385742826,-2.3226824133\H,-2.5264419448,-1.8346831925,-2.0835017363\H,

5.0875070917,-0.8062490167,-3.1136312822\H,1.1377520338,0.0761468286,-

3.2236043213\H,1.2126680129,-2.0989538428,0.6027232288\H,0.5263690145,

-4.1498285518,-2.9170102129\H,-1.65763668,-5.0339117589,-2.0813677978\

H,-2.4111738116,-4.3649009857,0.2286725963\H,-3.1905569557,1.252370285

1,3.4981209316\H,-5.7261052551,-2.846437129,1.4016588743\H,-6.03495597

69,-2.1941313368,2.9839128097\H,-1.059645652,-1.2300244273,3.267928457

5\H,-0.3306845173,-0.8651183534,1.7522277755\\Version=EM64L-G09RevA.02

\State=1-A\HF=-3501.9859683\S2=0.\S2-1=0.\S2A=0.\RMSD=5.824e-09\RMSF=7

.809e-06\ZeroPoint=0.5353613\Thermal=0.578045\Dipole=-2.1193165,-23.07

14026,-1.0163259\

Zero point energy

Zero-point correction= 0.535361 (Hartree/Particle)

Thermal correction to Energy= 0.578045

Thermal correction to Enthalpy= 0.578989

Thermal correction to Gibbs Free Energy= 0.460561

Sum of electronic and zero-point Energies= -3501.450607

Sum of electronic and thermal Energies= -3501.407923

Sum of electronic and thermal Enthalpies= -3501.406979

Sum of electronic and thermal Free Energies= -3501.525408

NADPH

1\1\GINC-COMPUTE-0-6\FOpt\UM062X\6-311++G(d,p)\C21H26N7O17P3(4-)\SNDAT

TA\26-Oct-2014\0\\#p opt Um062x/6-311++g(d,p) scrf=(solvent=water,read

,pcm) scf=tight geom=connectivity\\opt\\-4,1\P,-2.5056451938,-4.564446

6947,2.5304981665\P,-4.4320473981,1.8340833891,0.0114125956\P,-2.36461

68105,3.9318963743,0.3526827602\O,-1.8839710947,-2.0185171821,-1.71625

11287\O,1.7234813237,3.0214940269,1.8499869819\O,-2.1806585452,-4.4452

698638,0.8529666553\O,-4.1939375514,-3.7129616655,-0.9083750982\O,3.16

35361455,5.4066324868,2.8537192125\O,4.5092773097,4.7545484097,0.56592

2306\O,-4.0586890159,0.2502589378,0.1367152973\O,-0.9566080543,3.59930

35654,1.138178338\O,-2.9858438021,2.43638281,0.5168209212\O,-1.3950536

728,-3.7411769516,3.1830722273\O,-2.4143684929,-6.0680200143,2.7548083

161\O,-3.8992779355,-3.9586420348,2.6821250231\O,-4.63491124,2.2034613

836,-1.4245150999\O,-2.0388856949,4.2544657068,-1.0718778663\O,-5.4936

416539,2.1101153839,1.0237516563\O,-3.171802637,4.9048341756,1.1572630

122\O,-0.3803011101,0.9509779487,-1.8322323162\N,0.032829685,-2.874916

373,-0.6666253258\N,3.037273464,2.0218455372,0.1911501832\N,1.89639747

09,-1.8933713901,0.1112696061\N,1.0556702535,-4.5908006133,-2.07378146

42\N,3.4575973705,-4.4781559636,-2.0191091173\N,4.6222067868,-2.873810

1986,-0.8058070184\N,0.6634214114,-0.7174938478,-2.9212886402\C,-2.228

1714754,-3.1655420896,0.3210704178\C,-3.574557297,-2.6581443173,-0.192

3065098\C,-1.372913497,-3.0904008706,-0.9445564818\C,-3.1252508184,-1.

5512378045,-1.1451646978\C,2.3521510947,5.286781701,1.7045998192\C,3.1

397424831,4.479629652,0.6726261232\C,1.1696508761,4.3432254268,1.93878

9492\C,2.9760002349,3.0539317675,1.2058803833\C,-2.8664235113,-0.20267

75955,-0.494921652\C,0.0703692846,4.5521698739,0.9171373528\C,1.084924

1945,-3.5590950596,-1.2223030547\C,0.5914799388,-1.885999679,0.1102442

098\C,1.9386921419,1.6837521385,-0.5534301425\C,2.2241679208,-2.941421

5879,-0.7211140847\C,4.2512367709,1.3928065118,-0.0859381182\C,1.98140

58191,0.7948814138,-1.565539838\C,3.2773487154,0.1670167178,-2.0334943

77\C,4.3969347617,0.5264299606,-1.0896202704\C,3.4594774834,-3.4351811

441,-1.1784877289\C,2.2783955851,-4.9847879519,-2.4068225062\C,0.67128

47983,0.3726800318,-2.1002779314\H,-1.8575441632,-2.4335806808,1.05054

14292\H,-4.2072211705,-2.2964729264,0.6177112578\H,-1.4301062908,-4.02

84521917,-1.4993076349\H,-3.8438884789,-1.4328328502,-1.958328828\H,2.

0329923834,6.2629892632,1.3323096645\H,2.6421931629,4.5568230712,-0.29

90946116\H,0.7572986282,4.4570232193,2.9424590735\H,3.7843381642,2.856

5782622,1.9155374742\H,-2.5224303133,0.4973610868,-1.2555698619\H,-2.0

742180577,-0.2773749041,0.2558015883\H,-0.3141964015,5.5712676541,1.03

32788453\H,0.4464943348,4.4450198438,-0.1060174432\H,-5.0416033191,-3.

3989479277,-1.234064187\H,-0.0232287952,-1.1735908968,0.6391416594\H,2

.6657656803,5.8693712691,3.5333979471\H,4.6297865099,5.599884853,0.124

8542968\H,0.9953032922,2.1155918256,-0.2355560041\H,5.059252671,1.6509

472333,0.5853616204\H,3.1971289921,-0.9257399227,-2.0753885853\H,3.517

8108444,0.4809762152,-3.0558155698\H,5.3630004745,0.0603146459,-1.2314

631144\H,2.3390564077,-5.8252746274,-3.0887690868\H,5.4899573851,-3.22

53980203,-1.1744455867\H,4.62044922,-2.0435766603,-0.2330511043\H,-0.2

388424892,-1.1718038856,-3.0020084268\H,1.4738745065,-1.3144373866,-2.

9750654003\\Version=EM64L-G09RevA.02\State=1-A\HF=-3502.7044183\S2=0.\

S2-1=0.\S2A=0.\RMSD=1.411e-09\RMSF=1.266e-05\Dipole=21.5895501,7.89351

97,-8.5544091\

Zero point energy

Zero-point correction= 0.544135 (Hartree/Particle)

Thermal correction to Energy= 0.587920

Thermal correction to Enthalpy= 0.588865

Thermal correction to Gibbs Free Energy= 0.465889

Sum of electronic and zero-point Energies= -3502.160283

Sum of electronic and thermal Energies= -3502.116498

Sum of electronic and thermal Enthalpies= -3502.115554

Sum of electronic and thermal Free Energies= -3502.238529

Log Files S3. Log files from Gaussian09 Calculation: Optimization and frequency calculation at B3LYP/6-311++G(df,pd) level of theory

Phosphate (HPO42-)

1\1\GINC-LOCALHOST\Freq\UB3LYP\6-311++G(df,pd)\H1O4P1(2-)\SNDATTA\12-May-2015\0\\#P Geom=AllCheck Guess=TCheck SCRF=Check GenChk UB3LYP/6-31

1++G(df,pd) Freq\\phosphate opt freq\\-2,1\P,-0.1407080682,-0.02923391

77,0.0000013707\O,-0.2913731088,-0.8586781978,-1.2863924519\O,-0.29134

50902,-0.8586750305,1.2864005748\O,-0.9135630747,1.2953961464,0.000007

5849\O,1.4728661679,0.5049213818,-0.0000162718\H,2.0638991741,-0.25513

53821,-0.0000067652\\Version=EM64L-G09RevA.02\State=1-A\HF=-643.398818

8\S2=0.\S2-1=0.\S2A=0.\RMSD=7.085e-10\RMSF=1.589e-04\ZeroPoint=0.02494

63\Thermal=0.0300611\Dipole=1.8344664,-0.1911835,-0.0000067\

Zero point energy

Zero-point correction=0.024946 (Hartree/Particle)

Thermal correction to Energy= 0.030061

Thermal correction to Enthalpy= 0.031005

Thermal correction to Gibbs Free Energy= -0.003541

Sum of electronic and zero-point Energies= -643.373872

Sum of electronic and thermal Energies= -643.368758

Sum of electronic and thermal Enthalpies= -643.367814

Sum of electronic and thermal Free Energies= -643.402360

Water (H2O)

1\1\GINC-LOCALHOST\Freq\RB3LYP\6-311++G(df,pd)\H2O1\SNDATTA\12-May-201

5\0\\#N Geom=AllCheck Guess=TCheck SCRF=Check GenChk RB3LYP/6-311++G(d

f,pd) Freq\\water\\0,1\O,0.5381905645,1.0650571837,0.\H,1.5006529075,1

.1051363413,0.\H,0.2546943298,1.9856928258,0.\\Version=EM64L-G09RevA.0

2\State=1-A1\HF=-76.4686097\RMSD=1.342e-10\RMSF=2.710e-05\ZeroPoint=0.

0211871\Thermal=0.0240227\Dipole=0.5465544,0.7733566,0.\

Zero point energy

Zero-point correction= 0.021187 (Hartree/Particle)

Thermal correction to Energy= 0.024023

Thermal correction to Enthalpy= 0.024967

Thermal correction to Gibbs Free Energy= 0.003540

Sum of electronic and zero-point Energies= -76.447423

Sum of electronic and thermal Energies= -76.444587

Sum of electronic and thermal Enthalpies= -76.443643

Sum of electronic and thermal Free Energies= -76.465070

Full reference [28] of G09

Gaussian 09, Revision A.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Wallingford CT, 2009.

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