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

Deuterium incorporations from [2 H1 ]-(1R,2R) and [2 H1 ]-(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 [2 H5 ]-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.