NDLI: Design, synthesis and biological evaluation of sugar-derived esters, α-ketoesters and α-ketoamides as inhibitors for Mycobacterium tuberculosis antigen 85C

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Design, synthesis and biological evaluation of sugar-derived esters, α-ketoesters and α-ketoamides as inhibitors for Mycobacterium tuberculosis antigen 85C

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Molecular BioSystems Vol - 5 Issue - 8

Molecular BioSystems Vol - 5 Issue - 7

Molecular BioSystems Vol - 5 Issue - 6

Molecular BioSystems Vol - 5 Issue - 5

Molecular BioSystems Vol - 5 Issue - 4

Molecular BioSystems Vol - 5 Issue - 3

Molecular BioSystems Vol - 5 Issue - 2

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Molecular BioSystems Vol -3

Molecular BioSystems Vol -2

Design, synthesis and biological evaluation of sugar-derived esters, α-ketoesters and α-ketoamides as inhibitors for Mycobacterium tuberculosis antigen 85C

Content Provider	Royal Society of Chemistry (RSC)
Author	Umesiri, Francis E. Sucheck, Steven J. Boucau, Julie Ronning, Donald R. Sanki, Aditya K.
Copyright Year	2009
Abstract	Peptide-based 1,2-dicarbonyl compounds have emerged as potent inhibitors for serine proteases. Herein, we have designed and synthesized D-arabinose and D-trehalose-based esters, α-ketoesters and α-ketoamides, and evaluated their inhibitory activity against Mycobacterium tuberculosis (Mtb) antigen 85C (ag85C), an acyltransferase in the serine hydrolase superfamily. In addition the compounds were evaluated for the ability to inhibit the growth of Mycobacterium smegmatis ATCC 14 468, a non-pathogenic surrogate for Mtb. Among the synthetic analogs evaluated only the methyl ester1 derived from D-arabinose was found to inhibit the acyltransferase activity of ag85C (IC50 = 25 mM). Based on this weak inhibitory activity it was not surprising that none of the compounds inhibits the growth of M. smegmatis. In spite of the weak inhibitory activity of 1, X-ray crystallography on crystals of ag85C soaked with 1 suggested the formation of a covalent ester adduct between 1 and the Ser124 side chain hydroxyl moiety found within the catalytic site of ag85C; however, some of the active site electron density appears to result from bound glycerol. The lack of activity associated with the α-ketoester and α-ketoamide derivatives of D-trehalose may be the result of intramolecular cyclization of the α-keto moiety with the nearby C-4/4′ hydroxyls leading to the formation of stable bicyclo-ester and amide derivatives.
Starting Page	945
Ending Page	956
Page Count	12
File Format	HTM / HTML PDF
ISSN	1742206X
Volume Number	5
Issue Number	9
Journal	Molecular BioSystems
DOI	10.1039/b902284h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Serine Active site Mycobacterium smegmatis Glycerol Serine hydrolase Acyltransferase ATCC Antigen X-ray crystallography Ester Arabinose Hydroxy group Mycobacterium tuberculosis IC50 Covalent bond Amide Adduct
Content Type	Text
Resource Type	Article
Subject	Molecular Biology Biotechnology

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