Issue 19, 1989

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.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1989, 1421-1424

Biosynthesis of saxitoxin analogues: the origin and introduction mechanism of the side-chain carbon

S. Gupta, M. Norte and Y. Shimizu, J. Chem. Soc., Chem. Commun., 1989, 1421 DOI: 10.1039/C39890001421

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