The First One-Pot Synthesis of l‑7-Iodotryptophan from 7‑Iodoindole and Serine, and an Improved Synthesis of Other l‑7-Halotryptophans

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...

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Bibliographic Details
Published in:Organic letters 2014-05, Vol.16 (10), p.2622-2625
Main Authors: Smith, Duncan R. M, Willemse, Tom, Gkotsi, Danai S, Schepens, Wim, Maes, Bert U. W, Ballet, Steven, Goss, Rebecca J. M
Format: Article
Language:English
Subjects:
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
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5007746