Rapid, Stable, Chemoselective Labeling of Thiols with Julia–Kocieński‐like Reagents: A Serum‐Stable Alternative to Maleimide‐Based Protein Conjugation | Zendy

Toda Narihiro | Zendy; Asano Shigehiro | Zendy; Barbas Carlos F. | Zendy

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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.

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