Synthesis of a-factor peptide from Saccharomyces cerevisiae and photoactive analogues via Fmoc solid phase methodology

Daniel G. Mullen, Kelly Kyro, Melinda Hauser, Martin Gustavsson, Gianluigi Veglia, Jeffery M. Becker, Fred Naider, Mark D. Distefano

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

a-Factor from Saccharomyces cerevisiae is a farnesylated dodecapeptide involved in mating. The molecule binds to a G-protein coupled receptor and hence serves as a simple system for studying the interactions between prenylated molecules and their cognate receptors. Here, we describe the preparation of a-factor and two photoactive analogues via Fmoc solid-phase peptide synthesis using hydrazinobenzoyl AM NovaGel™ resin; the structure of the synthetic a-factor was confirmed by MS-MS analysis and NMR; the structures of the analogues were confirmed by MS-MS analysis. Using a yeast growth arrest assay, the analogues were found to have activity comparable to a-factor itself.

Original languageEnglish (US)
Pages (from-to)490-497
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume19
Issue number1
DOIs
StatePublished - Jan 1 2011

Bibliographical note

Funding Information:
The authors thank Bruce Witthuhn at University of Minnesota Center for Mass Spectrometry and Proteomics for assistance in performing the mass spectrometry experiments. This research was supported by the National Institutes of Health Grants GM58442 (M.D.D.) and GM22087 (J.M.B.).

Keywords

  • Benzophenone
  • C-Terminal methyl ester
  • Farnesyl
  • Peptide synthesis
  • Photoaffinity labeling
  • Prenylation
  • a-Factor

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