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Issue 38, 2017
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Incorporation of [2H1]-(1R,2R)- and [2H1]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus

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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.

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

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Publication details

The article was received on 30 Aug 2017, accepted on 11 Sep 2017 and first published on 11 Sep 2017


Article type: Communication
DOI: 10.1039/C7OB02163A
Citation: Org. Biomol. Chem., 2017,15, 8006-8008
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    Incorporation of [2H1]-(1R,2R)- and [2H1]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus

    X. Feng, N. Al Maharik, A. Bartholomé, J. E. Janso, U. Reilly and D. O'Hagan, Org. Biomol. Chem., 2017, 15, 8006
    DOI: 10.1039/C7OB02163A

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