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- W2293561206 endingPage "327" @default.
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- W2293561206 abstract "The rates of deamidation reactions of asparagine (Asn) residues which occur spontaneously and nonenzymatically in peptides and proteins via the succinimide intermediate are known to be strongly dependent on the nature of the following residue on the carboxyl side (Xxx). The formation of the succinimide intermediate is by far the fastest when Xxx is glycine (Gly), the smallest amino acid residue, while extremely slow when Xxx is bulky such as isoleucine (Ile) and valine (Val). In this respect, it is very interesting to note that the succinimide formation is definitely accelerated when Xxx is histidine (His) despite its large size. In this paper, we computationally show that, in an Asn–His sequence, the His side-chain imidazole group (in the neutral Nε-protonated form) can specifically catalyze the formation of the tetrahedral intermediate in the succinimide formation by mediating a proton transfer. The calculations were performed for Ace−Asn−His−Nme (Ace = acetyl, Nme = methylamino) as a model compound by the density functional theory with the B3LYP functional and the 6-31+G(d,p) basis set. We also show that the tetrahedral intermediate, once protonated at the NH2 group, easily releases an ammonia molecule to give the succinimide species." @default.
- W2293561206 created "2016-06-24" @default.
- W2293561206 creator A5011203970 @default.
- W2293561206 creator A5039619412 @default.
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- W2293561206 date "2016-03-09" @default.
- W2293561206 modified "2023-09-27" @default.
- W2293561206 title "A Computational Study of the Mechanism of Succinimide Formation in the Asn–His Sequence: Intramolecular Catalysis by the His Side Chain" @default.
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- W2293561206 doi "https://doi.org/10.3390/molecules21030327" @default.
- W2293561206 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6274526" @default.
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- W2293561206 hasPublicationYear "2016" @default.
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