J. Gebler, A. Woodside, C. Poulter
Sep 1, 1992
Citations
0
Influential Citations
68
Citations
Journal
Journal of the American Chemical Society
Abstract
Dimethylallyltryptophan (DMAT) synthase catalyzes the alkylation of L-tryptophan at C(4) by dimethylallyl diphosphate (DMAPP) in the first pathway-specific step in the biosynthesis of ergot alkaloids. The mechanism of the reaction was studied with analogs of both substrates. Five 7-substituted derivatives of N-acetyltryptophan (2, Z=OCH 3 , CH 3 , F, CF 3 , and NO 2 ) were synthesized. The L enantiomers of the free amino acids were obtained by selective hydrolysis of the racemate using aminoacylase from Aspergillus