Biosynthesis of saxitoxin analogues: the origin and introduction mechanism of the side-chain carbon
Abstract
Feeding experiments on Aphanizomenon flos-aquae have revealed that the side-chain carbon, the C-13, of neosaxitoxin is derived from methionine methyl group by an electrophilic attack of S-adenosylmethionine on a dehydro-intermediate, followed by a hydride migration and a proton loss, further elaboration of the side chain probably involves intermediacy of an aldehyde.