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Solid-phase synthesis of prenylcysteine analogs.

ABSTRACT: 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.

SUBMITTER: Donelson JL 

PROVIDER: S-EPMC2702710 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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Solid-phase synthesis of prenylcysteine analogs.

Donelson James L JL   Hodges-Loaiza Heather B HB   Henriksen Brian S BS   Hrycyna Christine A CA   Gibbs Richard A RA  

The Journal of organic chemistry 20090401 8

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 carbox  ...[more]

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