Supportinginformation
Table captions:
TableS1. Synthesisof compounds(6a-f, 8a-I, 10 and11)indifferentsolventsandreagents
TableS2. Listof Synthesizedα-acylaminoboronates
TableS3. Listof SynthesizedDipeptidylboronicacids
TableS1. Synthesis of compounds(6a-f, 8a-I, 10 and11)indifferentsolventsandreagents
S.No. / Solvent (20T) / Reagent / Temperature(°C) / Time(h) / Yield% / Impurity*1 / Toluene / Silica / 70-75 / 10 / 0 / 100
2 / DCM / TBTU / 0-25 / 5 / 70-75 / 18-20
3 / DCM / HBTU / 0-25 / 4 / 65-75 / 22-25
4 / DCM / PyBOP / 0-25 / 6 / 60-68 / 25-28
5 / DCM / EDC.HCl / 0-25 / 2 / 95-97 / 0.5-1.1
6 / DCM / DCC / 0-25 / 3 / 81-88 / 3-5.5
7 / Acetonitrile / EDC.HCl / 0-25 / 4 / 85-86 / 2.2-6.1
8 / Dioxan / EDC.HCl / 0-25 / 3 / 83-91 / 4-5.5
9 / THF / EDC.HCl / 0-25 / 2 / 81-90 / 6.5-7.5
10 / DMF / EDC.HCl / 0-25 / 1 / 88-91 / 1.1-2.2
*Impurity,inwhich Carbon-Boron bondcleavedas perHPLC purity
TableS2. Listof Synthesizedα-acylaminoboronates
NH R'' R'
CH3
CH3
Compound R’ R’’ MP Molecularformula Mol. Weight
-
O 86-88 C22H31BN2O5 414.3
+
O
Compound6a
I
Compound6b
O
200-202 C22H31BNIO3 495.2
O
30-32 C21H31BN2O3 370.2
Compound6c
Compound6e
Compound6d
Compound6f
N
O
H3C
O
Cl
O
N N
O
25-28 C23H34BNO3 383.3
110-112 C22H31BClNO3 403.75
55-57 C20H30BN3O3 371.28
TableS3. Listof SynthesizedDipeptidylboronicacids
RNH R'' R'
CH3
CH3
Compound R R’ R’’ MP
(OC)
Mol.Formula Mol.weight
Compound8a O
93-96 C21H26BN3O6 427.26
O N
O
Compound8c 104-106 C20H26BN3O4 383.25
N
O
Compound8d 73-75 C21H26BClN2O4 416.71
Cl
O
Compound I
8b
O
67-69 C21H26BIN2O4 508.15
Compound
8e
120-122 C34H46B2N6O8 688.39
Compound OH
8i
O
152-154 C21H27BN2O5 398.26
Compound
8f
Cl F N
Cl
O
105-107 C20H23
BCl2FN3O4
470.13
Compound
8g
Compound
8h
107-109 C23H30BN3O4 423.31
20-25 C15H25BN2O4S 340.25
H3C
CH
H3C
CH3
O
H3C
O O
H3C
CH
H3C
O
CH3
H3C O
CH3
H3C
H3C
CH3
H3C H3C
H2N
H3C
O
O
NH NH
CH3
3
B
NH O
H3C O
CH3
CH3
3
H3C
NH
H3C
NH
O H3C
NH
CH3
NH
O H3C
O
NH B
O
CH3
Compound10 Compound11
Figurecaptions:
Figure-2a: Hydrogen bonding interactions of compound 8e with ball and stick model of protein Compound 8e displayed in white color stick; hydrogen bonds are represented with blue dashed lines.
.
Figure-2b: Binding conformation of compound 8e and space occupied (green wire frame around ligand) in2XLN binding pocket.
Figure- 3a: Hydrogen bonding interactions of compound 8d with ball and stick model of protein, compound 8d displayed in white color stick; hydrogen bonds are represented with blue dashed lines.
Figure- 3b: Binding conformation of compound8d and space occupied (green wire frame around ligand) in2XLN binding pocket.
Figure -4a: Hydrogen bondinginteractions of compound8awith ball and stick model ofprotein, compound8adisplayedin white color stick; hydrogen bondsare represented with bluedashedlines.
Figure-4b: Binding conformation of compound 8a and space occupied (green wire frame around ligand) in2XLN binding pocket
Figure- 5a: Hydrogen bonding interactions of compound 8c with ball and stick model of protein, compound 8c displayed in white color stick; hydrogen bonds are represented with blue dashed lines.
Figure-5b:Binding conformation of compound 8c and space occupied (green wire frame around ligand) in2XLN binding pocket.
Figure-2a: Hydrogen bonding interactions of compound 8e with ball and stick model of protein Compound 8e displayed in white color stick; hydrogen bonds are represented with blue dashed lines.
Figure-2b: Binding conformation of compound 8e and space occupied (green wire frame around ligand) in2XLN binding pocket.
Figure- 3a: Hydrogen bonding interactions of compound 8d with ball and stick model of protein, compound 8d displayed in white color stick; hydrogen bonds are represented with blue dashed lines.
Figure- 3b: Binding conformation of compound8d and space occupied (green wire frame around ligand) in2XLN binding pocket.
Figure -4a: Hydrogen bondinginteractions of compound8awith ball and stick model ofprotein, compound8adisplayedin white color stick; hydrogen bondsare represented with bluedashedlines.
Figure-4b: Binding conformation of compound 8a and space occupied (green wire frame around ligand) in2XLN binding pocket
Figure- 5a: Hydrogen bonding interactions of compound 8c with ball and stick model of protein, compound 8c displayed in white color stick; hydrogen bonds are represented with blue dashed lines.
Figure-5b:Binding conformation of compound 8c and space occupied (green wire frame around ligand) in2XLN binding pocket.
ListofNMR spectra
1. 1H NMRof compound 6ain CDCl3
2. 1H NMRof compound6b in CDCl3
3. 1H NMRof compound 6cin CDCl3
4. 1H NMRof compound 6ein CDCl3
5. 1H NMRof compound 6fin CDCl3
6. 1H NMRof compound 8ain CDCl3
1H NMR of compound 6ain CDCl3
1H NMR of compound 6bin CDCl3
1H NMR of compound 6cin CDCl3
1H NMR of compound 6ein CDCl3
1H NMR of compound 6fin CDCl3
1H NMR of compound 8ain CDCl3