Catalyst-free site-selective cross-aldol bioconjugations. Issue 20 (27th September 2022)

• Record Type: Journal Article
• Authors: Yates, Nicholas D. J.; Akkad, Saeed; Noble, Amanda; Keenan, Tessa; Hatton, Natasha E.; Signoret, Nathalie; Fascione, Martin A.
• Is Part Of: Green chemistry. Volume 24:Issue 20(2022)
• Page Start: 8046
• Page End: 8053
• Publication Date: 2022-09-27
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc02292c
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : 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. Abstract : 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.