Total synthesis of the lipopeptide a-mating factor of Saccharomyces cerevisiae.
The a-mating factor of Saccharomyces cerevisiae was synthesized using both solution phase and solid phase strategies. Structure of the final peptide was confirmed using amino acid analysis, fast atom bombardment mass spectroscopy and 400 MHz proton NMR. The synthetic farnesylated dodecapeptide, YIIKGVFWDPAC (S-farnesyl) OCH3, exhibited chromatographic and spectroscopic properties identical to the natural pheromone and had significant biological activity at nanomolar concentrations.
Xue
C B
CB
Department of Chemistry, College of Staten Island, New York.
Caldwell
G A
GA
Becker
J M
JM
Naider
F
F
D000085:Acetates; D019342:Acetic Acid; D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D005656:Fungal Proteins / Q000138:chemical synthesis* / Q000494:pharmacology; D013058:Mass Spectrometry; D000072235:Mating Factor; D000432:Methanol; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D010675:Pheromones / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D012441:Saccharomyces cerevisiae / Q000254:growth & development; D012996:Solutions
D000085:Acetates; D005656:Fungal Proteins; D010455:Peptides; D010675:Pheromones; D012996:Solutions; D000072235:Mating Factor; D019342:Acetic Acid; D000432:Methanol