The biosynthesis of tropic acid: the stereochemical course of the mutase involved in hyoscyamine biosynthesis in Datura stramonium
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 2,p. 129-130
- https://doi.org/10.1039/c39950000129
Abstract
Incubation of (R,S)-DL-phenyl[2-3H]lactic acid with Datura stramonium generates hyoscyamine 2 with the tritium isotope located at C-3′ of the tropic acid ester moiety; the C-3′ hydroxymethyl group of 2 is converted into a chiral methyl group and is oxidised to generate chiral sodium acetate, with the (R) configuration (96% ee); the tritium is therefore located at the 3′-pro-S site of 2; it follows that the 3′-pro-R hydrogen is introduced with inversion of configuration by the mutase operating during hyoscyamine biosynthesis.Keywords
This publication has 0 references indexed in Scilit: