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Published on: January 26, 2012
Amino-Acid-Catalyzed Direct Aldol Bioconjugation
Tiauna S Howard1, Ryan D Cohen1,2, Ogonna Nwajiobi3
1Department of Chemistry and Biochemistry , Seton Hall University , South Orange , New Jersey 07079 , United States.
Abstract:
A site-specific bioconjugation was developed based on direct aldol coupling using amino-acid-derived organocatalysts. The functionalization exhibits fast kinetics and occurs under mild, biocompatible conditions (viz., aqueous media, moderate temperature, and neutral pH). The resulting bioconjugates were found to be stable toward abundant aldolase enzymes, as well as acidic and basic pH. The methodology was demonstrated through conjugation of a variety of small molecules, dyes, and peptides to proteins, including a single-domain antibody, which was then used for cellular imaging.
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