title: 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.
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, Purdue Cancer Center, Purdue University, West Lafayette, Indiana 47907, USA.
authors.forename: James L
authors.initials: JL
authors.lastname: Donelson
authors.forename: Heather B
authors.initials: HB
authors.lastname: Hodges-Loaiza
authors.forename: Brian S
authors.initials: BS
authors.lastname: Henriksen
authors.forename: Christine A
authors.initials: CA
authors.lastname: Hrycyna
authors.forename: Richard A
authors.initials: RA
authors.lastname: Gibbs