Synthesis of a-factor peptide from Saccharomyces cerevisiae and photoactive analogues via Fmoc solid phase methodology.
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.
Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, United States.
Daniel G
DG
Mullen
Kelly
K
Kyro
Melinda
M
Hauser
Martin
M
Gustavsson
Gianluigi
G
Veglia
Jeffery M
JM
Becker
Fred
F
Naider
Mark D
MD
Distefano
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D005656:Fungal Proteins / Q000096:biosynthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides / Q000737:chemistry*; D010777:Photochemistry; D012441:Saccharomyces cerevisiae / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry
D000596:Amino Acids; D005449:Fluorenes; D005656:Fungal Proteins; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides