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The synthesis of the cyclic antibacterial peptide Kawaguchipeptin B on 11 different DVB cross-linked PS resins

The synthesis of the cyclic antibacterial peptide Kawaguchipeptin B on 11 different DVB cross-linked PS resins
The synthesis of the cyclic antibacterial peptide Kawaguchipeptin B on 11 different DVB cross-linked PS resins
We report the first synthesis of the antibacterial peptide Kawaguchipeptin B. This was carried out on 11 different polystyrene resins ranging from 0.3 to 6.0% DVB cross-linking. The synthesis was accomplished using an Fmoc/Bu-t/Aloc strategy, with side chain resin attachment and a C-terminal allyl eater group for cyclisation. The syntheses of the linear and cyclic forms of the peptide were monitored and surprisingly showed that synthetic efficiency increased with increasing resin-cross linking.
solid-phase synthesis
0040-4039
5135-5139
Rana, Sunil
16726f81-3e09-45e4-b07b-944e7679e8ca
Dubuc, Julien
53bca9f2-7448-42a2-9f18-9ebecbd019aa
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900
White, Peter
536aaa93-447f-4103-ba6b-d424b51a5572
Rana, Sunil
16726f81-3e09-45e4-b07b-944e7679e8ca
Dubuc, Julien
53bca9f2-7448-42a2-9f18-9ebecbd019aa
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900
White, Peter
536aaa93-447f-4103-ba6b-d424b51a5572

Rana, Sunil, Dubuc, Julien, Bradley, Mark and White, Peter (2000) The synthesis of the cyclic antibacterial peptide Kawaguchipeptin B on 11 different DVB cross-linked PS resins. Tetrahedron Letters, 41 (26), 5135-5139. (doi:10.1016/S0040-4039(00)00754-1).

Record type: Article

Abstract

We report the first synthesis of the antibacterial peptide Kawaguchipeptin B. This was carried out on 11 different polystyrene resins ranging from 0.3 to 6.0% DVB cross-linking. The synthesis was accomplished using an Fmoc/Bu-t/Aloc strategy, with side chain resin attachment and a C-terminal allyl eater group for cyclisation. The syntheses of the linear and cyclic forms of the peptide were monitored and surprisingly showed that synthetic efficiency increased with increasing resin-cross linking.

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More information

Published date: 24 June 2000
Keywords: solid-phase synthesis

Identifiers

Local EPrints ID: 18867
URI: http://eprints.soton.ac.uk/id/eprint/18867
ISSN: 0040-4039
PURE UUID: 61fa81e6-f9ae-4368-8dd6-53a8c967a3a8

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Date deposited: 15 Dec 2005
Last modified: 15 Jul 2019 19:28

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Contributors

Author: Sunil Rana
Author: Julien Dubuc
Author: Mark Bradley
Author: Peter White

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