Solid-phase total synthesis of kahalalide A and related analogues
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).
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Description/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.
| Item Type: | Article |
|---|---|
| ISSNs: | 0022-2623 (print) |
| Related URLs: | |
| Keywords: | safety-catch linker, mollusk elysia-rufescens, peptide-synthesis, natural-products, cyclic-peptides, hiv-infection, tuberculosis, depsipeptide, cyclization, cleavage |
| Subjects: | R Medicine > RB Pathology Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 20734 |
| Date Deposited: | 01 Mar 2006 |
| Last Modified: | 25 Apr 2013 10:54 |
| Contributors: | Bourel-Bonnet, Line (Author) Rao, Karumanchi V. (Author) Hamann, Mark T. (Author) Ganesan, A. (Author) |
| Date: | 10 March 2005 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/20734 |
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