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Rapid, Stable, Chemoselective Labeling of Thiols with Julia–Kocieński‐like Reagents: A Serum‐Stable Alternative to Maleimide‐Based Protein Conjugation
Author(s) -
Toda Narihiro,
Asano Shigehiro,
Barbas Carlos F.
Publication year - 2013
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.201306241
Subject(s) - maleimide , chemoselectivity , chemistry , cysteine , conjugate , human serum albumin , thiol , reagent , click chemistry , combinatorial chemistry , iodoacetamide , biochemistry , organic chemistry , mathematical analysis , mathematics , enzyme , catalysis
Exquisite chemoselectivity for cysteine has been found for methylsulfonylphenyloxadiazole compounds under various buffer conditions. Furthermore, the resulting protein conjugates have superior stability to cysteine–maleimide conjugates in human plasma (HSA=human serum albumin, MBP‐C‐HA=maltose‐binding protein). This new thiol‐click reaction offers a new approach to generate stable protein conjugates and Pegylated proteins.