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Functionalization of protein hexahistidine tags by functional nanoreactors

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Abstract

A water-soluble Morita–Baylis–Hillman adduct (MBHA) derivative (3) was previously shown to self-assemble in a water environment into functional nanoreactors capable of performing multiple attacks and functionalization of N-acetylhexahistidine. In order to challenge this intriguing reactivity in a model protein more complex than N-acetylhexahistidine, the single-chain Fv antibody CRB0137 was characterized from the point of view of its structure and made to react with 3 in kinetics experiments. The results of these studies suggested that MBHA derivative 3 reacted typically with the amino acid residues of the CRB0137 hexahistidine tag leading to the formation of multi-PEGylated species. Overall, they demonstrate the viability of a new methodology for the site-specific PEGylation of engineered proteins bearing poly-histidine tags.

Graphical abstract: Functionalization of protein hexahistidine tags by functional nanoreactors

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Publication details

The article was received on 04 Jul 2019, accepted on 27 Oct 2019 and first published on 28 Oct 2019


Article type: Paper
DOI: 10.1039/C9NJ03463C
New J. Chem., 2019, Advance Article

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    Functionalization of protein hexahistidine tags by functional nanoreactors

    M. Paolino, M. Visintin, E. Margotti, M. Visentini, L. Salvini, A. Reale, V. Razzano, G. Giuliani, G. Caselli, F. Tavanti, M. C. Menziani and A. Cappelli, New J. Chem., 2019, Advance Article , DOI: 10.1039/C9NJ03463C

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