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J Biol Chem

Title:		Structure of Saccharomyces cerevisiae mating hormone a-factor. Identification of S-farnesyl cysteine as a structural component
Author(s):		Anderegg RJ; Betz R; Carr SA; Crabb JW; Duntze W;
Address:		"Department of Chemistry, University of Maine, Orono 04469"
Journal Title:		J Biol Chem
Year:		1988
Volume:		263
Issue:		34
Page Number:		18236 - 18240
DOI:
ISSN/ISBN:		0021-9258 (Print) 0021-9258 (Linking)
Abstract:		"Mating type a cells of the yeast Saccharomyces cerevisiae produce a mating hormone, the a-factor, that we have previously characterized as a very hydrophobic, modified dodecapeptide (Betz, R., Crabb, J. W., Meyer, H. E., Wittig, R., and Duntze, W. (1987) J. Biol. Chem. 262, 546-548). We have investigated the molecular structure in detail using mass spectrometry and proton NMR spectrometry of the intact hormone and authentic component molecules. Tandem mass spectrometry confirms the previously determined peptide sequence of the hormone and shows that it contains additional structural components with masses of 205 and 15 daltons. These were identified by proton NMR and mass spectrometry as a farnesyl (C15H25) residue and a terminal methyl ester group. The farnesyl moiety is attached to the sulfur atom of the carboxyl-terminal cysteine residue, as revealed by NMR of synthetic S-farnesyl cysteine methyl ester. The stereochemical configuration of the farnesyl moiety was determined to be trans,trans by comparison of gas chromatography retention times, mass spectra, and NMR spectra with those of standards. These results define the structure of a-factor as: (Sequence: see text). Replacement of the farnesyl by a methyl group leads to a partial reduction in specific biological activity of the a-factor, whereas hydrolysis of the carboxyl-terminal methyl ester causes a complete loss of activity"
Keywords:		"Amino Acid Sequence Chromatography, Gas Cysteine/*analogs & derivatives/analysis Magnetic Resonance Spectroscopy Mass Spectrometry Mating Factor *Peptides/isolation & purification *Pheromones Saccharomyces cerevisiae/*physiology;"
Notes:		"MedlineAnderegg, R J Betz, R Carr, S A Crabb, J W Duntze, W eng EY06603/EY/NEI NIH HHS/ GM32602/GM/NIGMS NIH HHS/ Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S. 1988/12/05 J Biol Chem. 1988 Dec 5; 263(34):18236-40"