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B6db references: 30673214

type Journal Article
authors Ushimaru R, Liu HW.
title Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics
journal J Am Chem Soc
Activity abmh
Family abmh
sel selected
ui 30673214
year (2019)
volume 141
number 6
pages 2211-2214
keywords doi: 10.1021/jacs.8b12565
abstract Albomycins are peptidyl thionucleoside natural products that display antimicrobial activity against clinically important patho-gens. Their structures are characterized by a thioheptose with atypical stereochemistry including a D-xylofuranose ring modified with a D-amino acid moiety. Herein it is demonstrated that AbmH is a pyridoxal 5'-phosphate (PLP)-dependent transal-dolase that catalyzes a threo-selective aldol-type reaction to gener-ate the thioheptose core with a D-ribofuranose ring and an L-amino acid moiety. The conversion of L- to D-amino acid con-figuration is catalyzed by the PLP-dependent epimerase AbmD. The D-ribo to D-xylo conversion of the thiofuranose ring appears according to gene deletion experiments to be mediated by AbmJ, which is annotated as a radical S-adenosyl-L-methionine (SAM) enzyme. These studies establish several key steps in the as-sembly of the thioheptose core during the biosynthesis of albomycins.
last changed 2019/03/12 09:52

B6db references