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Solid-phase total synthesis of kahalalide A and related analogues

Solid-phase total synthesis of kahalalide A and related analogues
Solid-phase total synthesis of kahalalide A and related analogues
The marine natural product kahalalide A, a cyclic depsipeptide, was prepared by total synthesis on solid-phase. A backbone cyclization strategy was followed, using the Kenner sulfonamide safety-catch linker. By NMR comparison of synthetic and naturally isolated material, the stereochemistry of the methylbutyrate side chain was established as (S). Several analogues were synthesized and tested for antimycobacterial activity. The results indicate that the alcohol functional group in the serine and threonine residues is important, while the methylbutyrate side chain can be replaced by an achiral hexanoate with an increase in activity.
safety-catch linker, mollusk elysia-rufescens, peptide-synthesis, natural-products, cyclic-peptides, hiv-infection, tuberculosis, depsipeptide, cyclization, cleavage
0022-2623
1330-1335
Bourel-Bonnet, Line
1b1e890c-17f3-4a67-bad8-d079eb9deaad
Rao, Karumanchi V.
df1aa064-a93d-404d-a05a-a5f721927b64
Hamann, Mark T.
2166adb0-9653-4683-82af-14168972c9d4
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9
Bourel-Bonnet, Line
1b1e890c-17f3-4a67-bad8-d079eb9deaad
Rao, Karumanchi V.
df1aa064-a93d-404d-a05a-a5f721927b64
Hamann, Mark T.
2166adb0-9653-4683-82af-14168972c9d4
Ganesan, A.
62aa5a87-9308-4383-8686-99726b6bcfb9

Bourel-Bonnet, Line, Rao, Karumanchi V., Hamann, Mark T. and Ganesan, A. (2005) Solid-phase total synthesis of kahalalide A and related analogues. Journal of Medicinal Chemistry, 48 (5), 1330-1335. (doi:10.1021/jm049841x).

Record type: Article

Abstract

The marine natural product kahalalide A, a cyclic depsipeptide, was prepared by total synthesis on solid-phase. A backbone cyclization strategy was followed, using the Kenner sulfonamide safety-catch linker. By NMR comparison of synthetic and naturally isolated material, the stereochemistry of the methylbutyrate side chain was established as (S). Several analogues were synthesized and tested for antimycobacterial activity. The results indicate that the alcohol functional group in the serine and threonine residues is important, while the methylbutyrate side chain can be replaced by an achiral hexanoate with an increase in activity.

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More information

Published date: 10 March 2005
Keywords: safety-catch linker, mollusk elysia-rufescens, peptide-synthesis, natural-products, cyclic-peptides, hiv-infection, tuberculosis, depsipeptide, cyclization, cleavage

Identifiers

Local EPrints ID: 20734
URI: http://eprints.soton.ac.uk/id/eprint/20734
ISSN: 0022-2623
PURE UUID: e17e74db-5d2c-43cc-afdd-d34013d62f3d

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Date deposited: 01 Mar 2006
Last modified: 15 Jul 2019 19:25

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Contributors

Author: Line Bourel-Bonnet
Author: Karumanchi V. Rao
Author: Mark T. Hamann
Author: A. Ganesan

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