Synthesis and biological activity of N epsilon-acyl derivatives of a Saccharomyces cerevisiae mating pheromone.
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.
D000818:Animals; D003227:Conjugation, Genetic / Q000187:drug effects; D010675:Pheromones / Q000138:chemical synthesis* / Q000494:pharmacology; D012441:Saccharomyces cerevisiae / Q000187:drug effects*; D013329:Structure-Activity Relationship
D010675:Pheromones