Stereochemistry of C-1 hydrogen exchange in the interconversion of trans,trans- and cis,trans-farnesols by soluble enzymes from tissue cultures of Andrographis paniculata

Abstract

When a cell-free system from A. paniculata tissue cultures isomerises trans,trans-farnesol (tt-F) to cis,trans-farnesol (ct-F), the 1-pro-R hydrogen of tt-F is retained and the 1-pro-S hydrogen lost; by contrast, conversion of ct-F proceeds with retention of the 1-pro-S and loss of the 1-pro-R hydrogen of ct-F.