title: Synthesis of peptides containing C-terminal methyl esters using trityl side-chain anchoring: application to the synthesis of a-factor and a-factor analogs.
abstract: A new cysteine anchoring method was developed for the synthesis of peptides containing C-terminal cysteine methyl esters. This method consists of attachment of Fmoc-Cys-OCH(3) to either 2-ClTrt-Cl or Trt-Cl resins (via the side-chain thiol) followed by preparation of the desired peptide using Fmoc-based SPPS. We applied this method to the synthesis of the mating pheromone a-factor and a 5-FAM labeled a-factor analog. The peptides were obtained with high yield and purity and were shown to be bioactive in a growth arrest assay.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Veronica
authors.initials: V
authors.lastname: Diaz-Rodriguez
authors.forename: Daniel G
authors.initials: DG
authors.lastname: Mullen
authors.forename: Elena
authors.initials: E
authors.lastname: Ganusova
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: Becker
authors.forename: Mark D
authors.initials: MD
authors.lastname: Distefano
mesh_terms: D000595:Amino Acid Sequence; D003545:Cysteine / Q000737:chemistry*; D004952:Esters; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004952:Esters; D010455:Peptides; D012724:Sex Attractants; D003545:Cysteine