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Rapid Preparation of Mycobacterium N‐ Glycolyl Lipid I and Lipid II Derivatives: A Biocatalytic Approach
Author(s) -
Chen KuoTing,
Kuan YeChing,
Fu WeiChen,
Liang PiHui,
Cheng TingJen R.,
Wong ChiHuey,
Cheng WeiChieh
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203251
Subject(s) - mycobacterium tuberculosis , biocatalysis , chemistry , mycobacterium , lipid a , computational biology , biochemistry , bacteria , combinatorial chemistry , tuberculosis , biology , catalysis , medicine , genetics , reaction mechanism , pathology
Breaking down barriers : A rapid, inexpensive preparation of the structurally complex mycobacterial N‐ glycolyl Lipid I, Lipid II, and their analogues from a range of different synthetic N‐ glycolyl and N ‐glycinyl Park's nucleotides is described (see scheme). The biotransformations were catalyzed by a readily available biocatalyst obtained from a bacterial cell‐free membrane fraction. The unnatural N ‐glycinyl Lipid II was found to be a substrate of Mycobacterium tuberculosis ( Mtb ) transglycosylase, PonA, and N‐ glycolyl Lipid I was a weak inhibitor against PonA.