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Synfacts 2009(7): 0815-0815  
DOI: 10.1055/s-0029-1217225
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Amide-Modified Farnesyl-cysteine Analogues

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
J. L. Donelson, H. B. Hodges-Loaiza, B. S. Henriksen, C. A. Hrycyna, R. A. Gibbs*
Purdue University, West Lafayette, USA
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Publikationsdatum:
22. Juni 2009 (online)

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Significance

An amide-modified farnesyl­cysteine (AMFC) library 6 was prepared via solid-phase synthesis. Thus, a farnesylcysteine-­supported resin 3 was prepared from Fmoc-Cys(St-Bu)OH (1) through S-alkylation with farnesyl chloride. The peptide condensation of 3 with various carboxylic acids 4 gave the resin-supported AMFC 5. The AMFC derivatives 6 were cleaved from the resin supports in 45-65% overall yield with over 90% purity (26 examples). Compound 8 was also prepared from 2, 2-phenoxybenzoic ­acid, and isobutenyl biphenyl derivative 9 in 40% yield.