Catalyst-free site-selective cross-aldol bioconjugations

The bioconjugation of proteins to small molecules serves as an invaluable tool for probing biological mechanisms and creating biomaterials. The most powerful bioconjugation stratagems are those which have rapid kinetics, are site-selective, can be conducted in aqueous solvent under mild conditions a...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2022-10, Vol.24 (2), p.846-853
Main Authors: Yates, Nicholas D. J, Akkad, Saeed, Noble, Amanda, Keenan, Tessa, Hatton, Natasha E, Signoret, Nathalie, Fascione, Martin A
Format: Article
Language:English
Subjects:
Aldehydes
Biocompatibility
Biomaterials
Biomedical materials
Catalysts
Coupling (molecular)
Green chemistry
Nanobodies
Prostate cancer
Proteins
Scalp
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Summary:The bioconjugation of proteins to small molecules serves as an invaluable tool for probing biological mechanisms and creating biomaterials. The most powerful bioconjugation stratagems are those which have rapid kinetics, are site-selective, can be conducted in aqueous solvent under mild conditions and do not require the use of additional potentially toxic catalysts. Herein we present spontaneous coupling via aldol ligation of proteins (SCALP) a catalyst-free "green" site-selective protein ligation between α-oxo aldehyde functionalised proteins and enolisable aldehyde probes at neutral pH, and demonstrate the utility of this system in the targeting of prostate cancer cells with functionalised nanobodies. We present catalyst-free "green" site-selective protein bioconjugations that utilise aldol condensations and are compatible with click chemistries, and construct a nanobody-derived bioconjugate capable of selectively labelling prostate cancer cells.
ISSN:1463-9262
1463-9270
DOI:10.1039/d2gc02292c