Intraannular savige-fontana reaction: One-step conversion of one class of monocyclic peptides into another class of bicyclic peptides
Intraannular savige-fontana reaction: One-step conversion of one class of monocyclic peptides into another class of bicyclic peptides
Cyclisation and cross-linking strategies are important for the synthesis of cyclic and bicyclic peptides. These macrolactams are of great interest due to their increased biological activity compared to linear analogues. Herein, we describe the synthesis of a cyclic peptide containing an Hpi toxicophore, reminiscent of phakellistatins and omphalotins. The first intraannular cross-linking of such a peptide is then presented: using neat TFA to catalyse a Savige-Fontana tryptathionylation, the Hpi-containing peptide is converted to a bicyclic amatoxin analogue. As such, this methodology represents an efficient cyclisation method for cross-linking peptides and exposes a heretofore unrealised relationship between two different classes of peptide natural products. This finding increases the degree of potential chemical space for library generation.
Cross-linking, Indole, Natural products, Oxidation, Peptides
3404-3409
May, Jonathan P.
b54a262b-9f32-4435-8866-3b9c495294f3
Perrin, David M.
12feb705-d3df-4f49-acf5-4283867ca47c
7 April 2008
May, Jonathan P.
b54a262b-9f32-4435-8866-3b9c495294f3
Perrin, David M.
12feb705-d3df-4f49-acf5-4283867ca47c
May, Jonathan P. and Perrin, David M.
(2008)
Intraannular savige-fontana reaction: One-step conversion of one class of monocyclic peptides into another class of bicyclic peptides.
Chemistry - A European Journal, 14 (11), .
(doi:10.1002/chem.200701088).
Abstract
Cyclisation and cross-linking strategies are important for the synthesis of cyclic and bicyclic peptides. These macrolactams are of great interest due to their increased biological activity compared to linear analogues. Herein, we describe the synthesis of a cyclic peptide containing an Hpi toxicophore, reminiscent of phakellistatins and omphalotins. The first intraannular cross-linking of such a peptide is then presented: using neat TFA to catalyse a Savige-Fontana tryptathionylation, the Hpi-containing peptide is converted to a bicyclic amatoxin analogue. As such, this methodology represents an efficient cyclisation method for cross-linking peptides and exposes a heretofore unrealised relationship between two different classes of peptide natural products. This finding increases the degree of potential chemical space for library generation.
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Published date: 7 April 2008
Keywords:
Cross-linking, Indole, Natural products, Oxidation, Peptides
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Local EPrints ID: 455580
URI: http://eprints.soton.ac.uk/id/eprint/455580
ISSN: 0947-6539
PURE UUID: b0e3639f-1c15-49a4-b4d5-f620f825b8a8
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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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