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.
Bibliographical noteFunding 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.).
- C-Terminal methyl ester
- Peptide synthesis
- Photoaffinity labeling