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Bioorthogonal Metalloporphyrin‐Catalyzed Selective Methionine Alkylation in the Lanthipeptide Nisin
Author(s) -
Maaskant Ruben V.,
Roelfes Gerard
Publication year - 2019
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201800493
Subject(s) - sulfonium , alkylation , nisin , chemistry , bioorthogonal chemistry , combinatorial chemistry , methionine , chemical biology , catalysis , biochemistry , organic chemistry , amino acid , antimicrobial , salt (chemistry) , click chemistry
Bioorthogonal catalytic modification of ribosomally synthesized and post‐translationally modified peptides (RiPPs) is a promising approach to obtaining novel antimicrobial peptides with improved properties and/or activities. Here, we present the serendipitous discovery of a selective and rapid method for the alkylation of methionines in the lanthipeptide nisin. Using carbenes, formed from water‐soluble metalloporphyrins and diazoacetates, methionines are alkylated to obtain sulfonium ions. The formed sulfonium ions are stable, but can be further reacted to obtain functionalized methionine analogues, expanding the toolbox of chemical posttranslational modification even further.