Nisin

Nisin is an inhibitory polycyclic peptide with 34 amino acid residues used as a food preservative. It contains the uncommon amino acids lanthionine, methyllanthionine, dehydroalanine and dehydro-amino-butyric acid. These special amino acids are synthesized by posttranslational enzymatic modifications. In these reactions a ribosomally synthesized 57-mer is converted to the final peptide. The unsaturated amino acids origin from serine and threonine.

Nisin is produced by fermentation using the bacterium Lactococcus lactis . Commercially it is obtained from natural substrates including milk and is not chemically synthesized. It is used in processed cheese production to extend shelf life by suppressing gram-positive spoilage and pathogenic bacteria. There are many other applications of this preservative in food and beverage production. Due to its highly selective spectrum of activity it is also employed as a selective agent in microbiological media for the isoloation of gram-negative bacteria, yeast and moulds. Subtilin and Epidermin are related to Nisin.

Further reading

• K. Fukase et. al., Tetrahedron Lett. 1988, 29, 7, 795. (Total synthesis)
• G. W. Buchman et. al., J. Biol. Chem. 1988, 263, 31, 16260. (Biosynthesis)