Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 19, Issue 1, Pages 490-497Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2010.11.006
Keywords
a-Factor; Benzophenone; C-Terminal methyl ester; Farnesyl; Peptide synthesis; Photoaffinity labeling; Prenylation
Funding
- National Institutes of Health [GM58442, GM22087]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM058842, R56GM022087, R01GM022087] Funding Source: NIH RePORTER
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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 (TM) 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. (C) 2010 Elsevier Ltd. All rights reserved.
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