PMID: 8944757Nov 1, 1996Paper

Structure and biological activity of chemically modified nisin A species

European Journal of Biochemistry
H S RollemaR J Siezen

Abstract

Nisin, a 34-residue peptide bacteriocin, contains the less common amino acids lanthionine, beta-methyl-lanthionine, dehydroalanine (Dha), and dehydrobutyrine (Dhb). Several chemically modified nisin A species were purified by reverse-phase HPLC and characterized by two-dimensional NMR and electrospray mass spectrometry. Five constituents, [2-hydroxy-Ala5]nisin, [Ile4-amide,pyruvyl-Leu6]des-Dha5-nisin, [Met(O)21]nisin, [Ser33]nisin, and nisin-(1-32)-peptide amide, were found in a commercial nisin sample. A further species, [2-hydroxy-Ala5]nisin-(1-32)-peptide amide, was obtained by freeze drying an acidic nisin solution. These compounds are formed by chemical modification of nisin: the addition of a water molecule to the dehydroalanine residues, which can lead to the cleavage of the polypeptide chain, or the oxidation of methionine residues. The 2-hydroxyalanine-containing products have a limited stability; they are spontaneously converted into the corresponding des-dehydroalanine derivatives. The growth-inhibiting activity of the modified nisins towards different bacteria was determined. The 2-hydroxyalanine-containing species and the des-dehydroalanine derivative show a strong reduction in biological activity as compared to na...Continue Reading

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Citations

May 12, 2001·FEMS Microbiology Reviews·O McAuliffeC Hill
Mar 21, 2012·Proceedings of the National Academy of Sciences of the United States of America·Neha GargWilfred A van der Donk
Jul 16, 2008·Applied and Environmental Microbiology·H Bart van den Berg van SaparoeaArnold J M Driessen
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Jun 26, 2018·Chemistry : a European Journal·A Dowine de Bruijn, Gerard Roelfes
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Aug 20, 2020·Chemical Communications : Chem Comm·Reinder H de Vries, Gerard Roelfes
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