Tryptathionine bridges in peptide synthesis
Tryptathionine bridges in peptide synthesis
The tryptathionine linkage is a crosslink formed between tryptophan and cysteine. This feature is characteristic of the bicyclic peptides: the phallotoxins and the amatoxins. These peptides both bind to protein folds of their respective targets (F-actin and RNA pol II, respectively) with extremely high affinities. Studies on these peptides have shown that the tryptathionine crosslink is essential for this binding affinity. Tryptathionines have been investigated for many years and several syntheses exist for their formation. In this review, we report on the various methodologies employed in tryptathionine synthesis, and discuss some of the advantages and disadvantages associated with each of them.
Amatoxin, Crosslink, Natural product, Phallotoxin, Tryptathionine
714-724
May, Jonathan P.
b54a262b-9f32-4435-8866-3b9c495294f3
Perrin, David M.
12feb705-d3df-4f49-acf5-4283867ca47c
11 July 2007
May, Jonathan P.
b54a262b-9f32-4435-8866-3b9c495294f3
Perrin, David M.
12feb705-d3df-4f49-acf5-4283867ca47c
May, Jonathan P. and Perrin, David M.
(2007)
Tryptathionine bridges in peptide synthesis.
Peptide Science, 88 (5), .
(doi:10.1002/bip.20807).
Abstract
The tryptathionine linkage is a crosslink formed between tryptophan and cysteine. This feature is characteristic of the bicyclic peptides: the phallotoxins and the amatoxins. These peptides both bind to protein folds of their respective targets (F-actin and RNA pol II, respectively) with extremely high affinities. Studies on these peptides have shown that the tryptathionine crosslink is essential for this binding affinity. Tryptathionines have been investigated for many years and several syntheses exist for their formation. In this review, we report on the various methodologies employed in tryptathionine synthesis, and discuss some of the advantages and disadvantages associated with each of them.
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Accepted/In Press date: 21 June 2007
Published date: 11 July 2007
Keywords:
Amatoxin, Crosslink, Natural product, Phallotoxin, Tryptathionine
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Local EPrints ID: 455582
URI: http://eprints.soton.ac.uk/id/eprint/455582
ISSN: 2475-8817
PURE UUID: 7f3c5a3b-04b9-4f99-acef-77ae3fdb74bd
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Date deposited: 28 Mar 2022 16:38
Last modified: 17 Mar 2024 03:53
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Author:
David M. Perrin
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