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Kinetics of Thiol/Disulfide Exchange Correlate Weakly with the Restoring Force in the Disulfide Moiety
Author(s) -
Kucharski Timothy J.,
Huang Zhen,
Yang QingZheng,
Tian Yancong,
Rubin Nicholas C.,
Concepcion Carlos D.,
Boulatov Roman
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901511
Subject(s) - moiety , thiol , disulfide bond , kinetics , chemistry , stereochemistry , organic chemistry , biochemistry , physics , quantum mechanics
S‐S‐Stretch! A series of increasingly strained macrocyclic disulfides investigated experimentally and by high‐level DFT calculations reveals that the kinetics of thiol/disulfide exchange are independent of the restoring force in the disulfide moiety. This finding is consistent with the S N 2 mechanism of thiol/disulfide exchange and lends insight into the acceleration of disulfide reduction upon stretching of certain proteins.