Solid-Phase Synthesis of Prenylcysteine Analogs

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• 作者：James L. Donelson ; Heather B. Hodges-Loaiza ; Brian S. Henriksen ; Christine A. Hrycyna ; Richard A. Gibbs
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：April 17, 2009
• 年：2009
• 卷：74
• 期：8
• 页码：2975-2981
• 全文大小：262K
• 年卷期：v.74,no.8(April 17, 2009)
• ISSN：1520-6904

文摘

Prenylcysteine derivatives are of interest for a variety of different biological reasons, including probing the CaaX protein processing pathway. A solid-phase synthesis protocol for the preparation of prenylcysteines using 2-chlorotrityl chloride resin as a solid support has been developed. A series of novel amide-modified farnesylcysteine analogs were synthesized in both high purity and yield under mild conditions. The farnesylcysteine analogs were evaluated using human isoprenylcysteine carboxyl methyltransferase as a biological target, and several new inhibitors, one with significantly enhanced potency, were identified.