| Title: | Synthesis of biologically active analogs of the dodecapeptide a-factor mating pheromone of Saccharomyces cerevisiae |
| Author(s): | Ewenson A; Marcus S; Becker JM; Naider F; |
| Address: | "Department of Chemistry, College of Staten Island, City University of New York" |
| DOI: | 10.1111/j.1399-3011.1990.tb00944.x |
| ISSN/ISBN: | 0367-8377 (Print) 0367-8377 (Linking) |
| Abstract: | "A number of dodecapeptides with the sequence YIIKGVFWDPAC were synthesized using solid phase peptide synthesis. The purity of the crude cleavage product was found to be directly related to the cysteine protecting group and the conditions employed for cleavage of the peptide from the resin. When 4-methyl-benzyl cysteine was used, complete deprotection was only achieved with low-high HF conditions at temperatures of 10 degrees-25 degrees, whereas milder conditions could be used for dodecapeptides containing ethyl cysteine or acetamidomethyl cysteine. In several syntheses the biological activity of the crude cleavage product greatly exceeded the biological activity of a purified major peptide component. The high activity found in the crude cleavage peptide was probably due to minor peptide side products in which the cysteine sulfur was alkylated by hydrophobic species during HF treatment. Two dodecapeptides, YIIKGVFWDPAC and YIIKGFWDPAC(Ethyl), had significant a-factor activity against MAT alpha strains of Saccharomyces cerevisiae. These peptides represent the first synthetic analogs with a-factor activity" |
| Keywords: | "Amino Acid Sequence Chemical Phenomena Chemistry, Physical Cysteine Hydrofluoric Acid Mating Factor Mesylates Molecular Sequence Data Oligopeptides/*chemical synthesis/pharmacology Peptides/*chemical synthesis Pheromones Saccharomyces cerevisiae/*analysis;" |
| Notes: | "MedlineEwenson, A Marcus, S Becker, J M Naider, F eng GM22086/GM/NIGMS NIH HHS/ GM22087/GM/NIGMS NIH HHS/ Comparative Study Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S. Denmark 1990/03/01 Int J Pept Protein Res. 1990 Mar; 35(3):241-8. doi: 10.1111/j.1399-3011.1990.tb00944.x" |
