Enzymatic Synthesis of Bromo- and Chlorocarbazoles and Elucidation of Their Structures

SUPPLEMENTARY MATERIAL

Enzymatic synthesis of bromo- and chlorocarbazoles and elucidation of their structures by molecular modeling

John Mumbo 1,2,3,4*, Dieter Lenoir1, Bernhard Henkelmann1, Karl-Werner Schramm1,2**

1.  Helmholtz Zentrum München-German Research Center for Environmental Health (GmbH),
Molecular EXposomics, Ingolstädter Landstraße 1, 85764 Neuherberg, Germany
email: * , **

2.  Department für Biowissenschaftliche Grundlagen, TUM-Technische Universität München,
Weihenstephaner Steig 23, 85350 Freising, Germany
email: *, **

3.  Department of Chemistry, Maseno University, Private Bag, Maseno, Kenya

4.  National Environment Management Authority, P.O. Box 67839-00200, Nairobi, Kenya

Supplementary Material

Page Material

S-2 Figure S1. Gas chromatogram of (A) bromocarbazoles and (B) chlorocarbazoles
detected during halogenation of carbazole by chloroperoxidase of Caldariomyces
fumago.

S-3 to S-6 Figure S2 to Figure S5. Mass spectra of mono-, di-, tri- and tetra-bromocarbazoles

S-7 to S-9 Figure S6 to Figure S8. Mass spectra of di-, tri- and tetra-chlorocarbazoles

S-10 Table S1 Substrate concentrations in environmental water samples

S-11 Table S2. Log Kow values of carbazole, bromo- and chlorocarbazoles

Fig. S1 Gas chromatograms of bromocarbazoles (A) from left to right and chlorocarbazoles (B) also from left to right. The synthesis followed the same trend with the mono- and dihalogenated carbazoles formed in the 2:2:1 and 1:10:3 reaction ratio treatments while mono-, di-, tri- and tetrahalogenated carbazoles were all formed in 1:1000:50 reaction ratio treatments.

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Fig. S2 Mass spectrum of monobromocarbazole

Fig. S3 Mass spectrum of dibromocarbazole

Fig. S4 Mass spectrum of tribromocarbazole

Fig. S5 Mass spectrum of tetrabromocarbazole

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Fig. S6 Mass spectrum of dichlorocarbazole

Fig. S7 Mass spectrum of trichlorocarbazole

Fig. S8 Mass spectrum of tetrachlorocarbazole

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Table S1 Substrate concentrations in environmental water samples

Table S2 Log Kow values of carbazole, bromo- and chlorocarbazoles

Source: National Centre for Biotechnology Information (NCBI), US National library of medicine

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