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Rapid Nitrogen Inversion Pathway in the cis / trans Isomerization of Selenoxo Peptide Bonds
Author(s) -
Huang Yun,
Jahreis Günther,
Lücke Christian,
Fischer Gunter
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203721
Subject(s) - isomerization , tautomer , chemistry , nitrogen inversion , peptide bond , peptide , nitrogen , oligopeptide , stereochemistry , ion , computational chemistry , catalysis , organic chemistry , biochemistry
Two sides to a nitrogen : The cis to trans isomerization of selenoxo peptides in alkaline conditions is rationalized in terms of rapid nitrogen inversion of the tautomeric selenoimidate anion [C(Se − )N] (see scheme), which increases the isomerization rate by about 30‐fold as compared to the rotational pathway of the [CSeNH] form. The current work identifies the imino tautomer of a selenoxo peptide bond as a potential means to enhance oligopeptide backbone dynamics in a site‐specific manner.
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