Rapid Preparation of Mycobacterium N-Glycolyl Lipid I and Lipid II Derivatives: A Biocatalytic Approach

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...

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Bibliographic Details
Published in:Chemistry : a European journal 2013-01, Vol.19 (3), p.834-838
Main Authors: Chen, Kuo-Ting, Kuan, Ye-Ching, Fu, Wei-Chen, Liang, Pi-Hui, Cheng, Ting-Jen R., Wong, Chi-Huey, Cheng, Wei-Chieh
Format: Article
Language:English
Subjects:
antibiotics
Bacteria
Bacterial Outer Membrane Proteins - metabolism
Bacterial Proteins - metabolism
Barriers
Biocatalysis
Biotransformation
Breaking down
Chemistry
Derivatives
Glycolipids - biosynthesis
Glycolipids - chemistry
Glycolipids - metabolism
inhibitors
Lipids
Molecular Structure
Mycobacterium tuberculosis
Mycobacterium tuberculosis - chemistry
Mycobacterium tuberculosis - enzymology
Mycobacterium tuberculosis - metabolism
N-Acetylglucosaminyltransferases - metabolism
Nucleotides
synthetic methods
Transferases - metabolism
transglycosylase
Tuberculosis
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Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201203251