| Title: | Synthesis and biological activity of N epsilon-acyl derivatives of a Saccharomyces cerevisiae mating pheromone |
| Author(s): | Shenbagamurthi P; Kundu B; Becker JM; Naider F; |
| DOI: | 10.1111/j.1399-3011.1985.tb02163.x |
| ISSN/ISBN: | 0367-8377 (Print) 0367-8377 (Linking) |
| Abstract: | "We report a general method for acylation of the N epsilon-amino group of the lysyl residue in peptides. The procedure involves acylation using p-nitrophenyl esters and 1-hydroxybenzotriazole in organic solvents to yield a series of fatty acyl mating pheromones of Saccharomyces cerevisiae. The fatty acyl group does not influence coupling of peptide fragments. Biological activities of the synthesized alpha-factor mating pheromones derivatized with acetyl, butyryl, caprylyl and lauryl groups are nearly equivalent to the activity of unacylated alpha-factor. The N epsilon-stearyl-alpha-factor is biologically inactive. The procedures reported in this communication can be used to increase hydrophobicity of lysine-containing peptides when the lysyl group is not essential for activity" |
| Keywords: | "Animals Conjugation, Genetic/drug effects Pheromones/*chemical synthesis/pharmacology Saccharomyces cerevisiae/*drug effects Structure-Activity Relationship;" |
| Notes: | "MedlineShenbagamurthi, P Kundu, B Becker, J M Naider, F eng GM 22086/GM/NIGMS NIH HHS/ GM22087/GM/NIGMS NIH HHS/ Comparative Study Research Support, U.S. Gov't, Non-P.H.S. Research Support, U.S. Gov't, P.H.S. Denmark 1985/02/01 Int J Pept Protein Res. 1985 Feb; 25(2):187-96. doi: 10.1111/j.1399-3011.1985.tb02163.x" |
