Biosynthesis of acaterin: Metabolic fate of sn-3 hydrogens of glycerol during the formation of 4-dehydroacaterin

Article abstract of DOI:10.1016/S0040-4039(99)00681-4

The metabolic fate of the pro-R and pro-S hydrogens at the sn-C-3 position of glycerol during the formation of 4-dehydroacaterin has been investigated using Pseudomonas sp. A92. Feeding studies of sn-(3R)- and sn-(3S)-(3-²H)glycerols revealed that 5E hydrogen of 4-dehydroacaterin originates mainly from pro-R hydrogen at sn-C-3 of glycerol, while 5Z hydrogen comes mainly from pro-S. These results ruled out pyruvate and lactate as the immediate precursor of the C₃ branched unit of acaterin, and suggest 1,3-bisphosphoglyceric acid or its biological equivalent as the precursor.