Open AccessAmino-Acid-Catalyzed Direct Aldol Bioconjugation
Author(s) -
Tiauna S. Howard,
Ryan D. Cohen,
Ogonwajiobi,
Zilma P. Muneeswaran,
Yonnette E. Sim,
Neelam Lahankar,
Johannes T.H. Yeh,
Monika Raj
Publication year - 2018
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.8b02265
Subject(s) - bioconjugation , chemistry , aldol reaction , aldolase a , combinatorial chemistry , surface modification , catalysis , amino acid , enzyme , small molecule , biochemistry
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.