@inbook{88350b196635438b95dcc087aaff9575,
title = "Peptide backbone modifications in lanthipeptides",
abstract = "Lanthipeptides are a class of ribosomally synthesized and posttranslationally modified peptide (RiPP) natural products characterized by the presence of lanthionine and methyllanthionine. During the maturation of select lanthipeptides, five different alterations have been observed to the chemical structure of the peptide backbone. First, dehydratases generate dehydroalanine and dehydrobutyrine from Ser or Thr residues, respectively. A second example of introduction of unsaturation is the oxidative decarboxylation of C-terminal Cys residues catalyzed by the decarboxylase LanD. Both modifications result in loss of chirality at the α-carbon of the amino acid residues. Attack of a cysteine thiol onto a dehydrated amino acid results in thioether crosslink formation with either inversion or retention of the L-stereochemical configuration at the α-carbon of former Ser and Thr residues. A fourth modification of the protein backbone is the hydrogenation of dehydroamino acids to afford D-amino acids catalyzed by NAD(P)H-dependent reductases. A fifth modification is the conversion of Asp to isoAsp. Herein, the methods used to produce and characterize the lanthipeptide bicereucin will be described in detail along with a brief overview of other lanthipeptides.",
keywords = "D-amino acids, Dehydroalanine, Dehydrobutyrine, Isoaspartate, Lanthionine",
author = "Ayikpoe, {Richard S.} and {van der Donk}, {Wilfred A.}",
note = "Funding Information: The authors thank the Howard Hughes Medical Institute and the National Institutes of Health (R37 GM 058822 to W.A.v.d.D) for the continued support of our research on lanthipeptides. We also thank former members of our laboratory that worked out some of the procedures described herein (Dr. Liujie Huo and Dr. Manuel Ortega). Publisher Copyright: {\textcopyright} 2021 Elsevier Inc.",
year = "2021",
month = jan,
doi = "10.1016/bs.mie.2021.04.012",
language = "English (US)",
isbn = "9780128212530",
series = "Methods in Enzymology",
publisher = "Academic Press Inc.",
pages = "573--621",
editor = "Petersson, {E. James}",
booktitle = "Synthetic and Enzymatic Modifications of the Peptide Backbone",
address = "United States",
}