The first one-pot synthesis of L-7-iodotryptophan from 7-iodoindole and serine, and an improved synthesis of other L-7-halotryptophans

Duncan R M Smith; Tom Willemse; Danai S Gkotsi; Wim Schepens; Bert U W Maes; Steven Ballet; Rebecca J M Goss

doi:10.1021/ol5007746

The first one-pot synthesis of L-7-iodotryptophan from 7-iodoindole and serine, and an improved synthesis of other L-7-halotryptophans

Org Lett. 2014 May 16;16(10):2622-5. doi: 10.1021/ol5007746. Epub 2014 May 7.

Authors

Duncan R M Smith¹, Tom Willemse, Danai S Gkotsi, Wim Schepens, Bert U W Maes, Steven Ballet, Rebecca J M Goss

Affiliation

¹ School of Chemistry and BSRC, University of St. Andrews , St. Andrews, KY16 9ST, U.K.

PMID: 24805161
DOI: 10.1021/ol5007746

Abstract

A simple and scalable one-pot biotransformation enables direct access to L-halotryptophans, including L-7-iodotryptophan, from the corresponding haloindoles. The biotransformation utilizes an easy to prepare bacterial cell lysate that may be stored as the lyophilizate for several months and utilized as a catalyst as and when required.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biotransformation
Catalysis
Hydrocarbons, Iodinated / chemical synthesis*
Hydrocarbons, Iodinated / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry*
Molecular Structure
Serine / chemistry*
Stereoisomerism
Tryptophan / analogs & derivatives*
Tryptophan / chemical synthesis*
Tryptophan / chemistry
Tryptophan Synthase / metabolism

Substances

Hydrocarbons, Iodinated
Indoles
Serine
Tryptophan
Tryptophan Synthase