Incorporation of [2H1]-(1R,2R)- and [2H1]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus

Xuan Feng, Nawaf Al Maharik, Axel Bartholome, Jeffrey E. Janso, Usa Reilly, David O'Hagan

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Abstract

Deuterium incorporations from [2H1]-(1R,2R) and [2H1]-(1S,2R) glycerols into the fluorine containing antibiotic nucleocidin, in Streptomyces calvus indicate that one deuterium atom is incorporated at the C-5′ site of nucleocidin from each of these isotopomers of glycerol. Two deuteriums become incorporated at C-5′ of nucleocidin after a feeding experiment with [2H5]-glycerol. These observations indicate that there is no obligate oxidation of the pro-R hydroxymethyl group of glycerol as it progresses through the pentose phosphate pathway and becomes incorporated into the fluorinated antibiotic.
Original languageEnglish
Pages (from-to)8006-8008
JournalOrganic & Biomolecular Chemistry
Volume15
Issue number38
Early online date11 Sept 2017
DOIs
Publication statusPublished - 14 Oct 2017

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