ORGN 308 |
| Callipeltin B, a macrocyclic depsipeptide isolated from the New Caledonian sponge Callipelta Sp., exhibits broad spectrum antitumor activity. Apart from its interesting biological activity, it is a structurally challenging synthetic target. It has several non-proteinogenic amino acids, of which β-methoxytyrosine residue is one. This β-methoxytyrosine residue is conserved in Callipeltin A-E and also in similar class of depsipeptide molecules like Papuamides A-D and Neamphamide A. The work presented herein involves a solid phase synthesis of Callipeltin B by a side chain attachment of the N-methylglutamine to a Sieber resin, on-resin esterification and cyclization. To determine the role of β-Methoxytyrosine in the biological activity of Callipeltin B, an analogue with D-Tyr in place of (R)-β-OMe-D-Tyr was synthesized and tested for antitumor activity.
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Combinatorial, Parallel, and Solid-Phase Chemistry
1:00 PM-5:20 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- C302, Oral
Division of Organic Chemistry |
