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Amino-Acid-Catalyzed Direct Aldol Bioconjugation.

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.

SUBMITTER: Howard TS

PROVIDER: S-EPMC7751349 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Amino-Acid-Catalyzed Direct Aldol Bioconjugation.

Howard Tiauna S TS Cohen Ryan D RD Nwajiobi Ogonna O Muneeswaran Zilma P ZP Sim Yonnette E YE Lahankar Neelam N NN Yeh Johannes T-H JT Raj Monika M

Organic letters 20180820 17

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 pr ...[more]

PMID: 30125118

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