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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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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.[1]

References

  1. Synthesis and biological activity of N epsilon-acyl derivatives of a Saccharomyces cerevisiae mating pheromone. Shenbagamurthi, P., Kundu, B., Becker, J.M., Naider, F. Int. J. Pept. Protein Res. (1985) [Pubmed]
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