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Ring-Closing Metathesis in the Synthesis of Biologically Active Peptidomimetics of Apicidin A

✍ Scribed by Prashant H. Deshmukh; Carsten Schulz-Fademrecht; Panayiotis A. Procopiou; David A. Vigushin; R. Charles Coombes; Anthony G. M. Barrett

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 161 KB
Volume: 349
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200600421

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✦ Synopsis

Abstract

Syntheses of novel 16‐membered macrocyclic peptidomimetics are reported, which employ iterative peptide coupling followed by high yielding ring‐closing metathesis (RCM) as the key cyclization step. The target macrocyclic compounds include examples containing a (2__S__)‐amino‐8‐oxodecanoic acid (Aoda) residue as analogues of apicidin A, a known potent histone deacetylase (HDAC) inhibitor. These showed modest levels of biological activity as HDAC inhibitors.

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Generous financial support by the MPG, the Fonds der Chemischen Industrie, and the Merck Research Council is gratefully acknowledged. We thank Dr. D. De Souza for helpful comments and discussions and Dipl.-Chem. J. T. Jensen for preliminary experiments on the synthesis of the acid segment.