The synthesis of dehydrotryptophan and dehydrotryptophan-containing peptides

Harveen Kaur; Amanda M. Heapy; Margaret A. Brimble

doi:10.1039/C1OB05777D

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Organic & Biomolecular Chemistry

Issue 17, 2011

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The synthesis of dehydrotryptophan and dehydrotryptophan-containing peptides

Harveen Kaur,^a^b Amanda M. Heapy^a^b and Margaret A. Brimble*^a^b

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School of Chemical Sciences, The University of Auckland, 23 Symonds St, Auckland, New Zealand
E-mail: m.brimble@auckland.ac.nz

Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland, New Zealand

Org. Biomol. Chem., 2011,9, 5897-5907

DOI: 10.1039/C1OB05777D
Received 18 May 2011, Accepted 24 Jun 2011
First published online 08 Jul 2011

This article is part of themed collection: Organic & Biomolecular Chemistry 2011 review articles

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Abstract
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Dehydrotryptophan and its derivatives are non-proteinogenic amino acids commonly found in peptide-based natural products produced by microorganisms, marine organisms and plants. These non-proteinogenic amino acids are found in secondary metabolites and are formed by post translational modification processes. Although comprehensive reviews on the synthesis of dehydroamino acids are available, this perspective focuses solely on methods to synthesise the dehydrotryptophan-containing segment of naturally occurring peptides, amino acids and their derivatives.

Abstract from Methods in Organic Synthesis 2012

A review, with 95 references, focusing on the synthesis of the dehydrotryptophan-containing segments of natural products, naturally occurring peptides, amino acids and their derivatives.

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