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Protein Modification by Strain‐Promoted Alkyne–Nitrone Cycloaddition
Author(s) -
Ning Xinghai,
Temming Rinske P.,
Dommerholt Jan,
Guo Jun,
Ania Daniel B.,
Debets Marjoke F.,
Wolfert Margreet A.,
Boons GeertJan,
van Delft Floris L.
Publication year - 2010
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.201000408
Subject(s) - bioorthogonal chemistry , cycloaddition , chemistry , alkyne , combinatorial chemistry , azide , click chemistry , biomolecule , catalysis , organic chemistry , biochemistry
Quicker and slicker : An efficient metal‐free 1,3‐dipolar cycloaddition of dibenzocyclooctynes with nitrones proceeded with rate constants of up to 39 M −1 s −1 , or up to 300 times faster than similar reactions with azides. This strategy is useful for the site‐specific N‐terminal modification of peptides and proteins (see scheme).