Incorporation of [2H1]-(1R,2R)- and [2H1]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvusElectronic supplementary information (ESI) available. See DOI: 10.1039/c7ob02163a

• Main Authors: Feng, Xuan, Al Maharik, Nawaf, Bartholomé, Axel, Janso, Jeffrey E, Reilly, Usa, O'Hagan, David
• Format: Article
• Language: English
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c7ob02163a

Deuterium incorporations from [ 2 H 1 ]-(1 R ,2 R ) and [ 2 H 1 ]-(1 S ,2 R ) 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 [ 2 H 5 ]-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. Both pro-R hydroxylmethyl hydrogens of glycerol are incorporated into nucleocidin in Streptomyces calvus .