PubAg

Main content area

Regioselectivity of the Oxidative C–S Bond Formation in Ergothioneine and Ovothiol Biosyntheses

Author:
Song, Heng, Leninger, Maureen, Lee, Norman, Liu, Pinghua
Source:
Organic letters 2013 v.15 no.18 pp. 4854-4857
ISSN:
1523-7052
Subject:
biochemical pathways, chemical bonding, chemical reactions, chemical structure, cysteine, enzymes, histidine, regioselectivity
Abstract:
Ergothioneine (5) and ovothiol (8) are two novel thiol-containing natural products. Their C–S bonds are formed by oxidative coupling reactions catalyzed by EgtB and OvoA enzymes, respectively. In this work, it was discovered that in addition to catalyzing the oxidative coupling between histidine and cysteine (1 → 6 conversion), OvoA can also catalyze a direct oxidative coupling between hercynine (2) and cysteine (2 → 4 conversion), which can shorten the ergothioneine biosynthetic pathway by two steps.
Agid:
5785958