Issue 28, 2021

A 2-formylphenylboronic acid (2FPBA)-maleimide crosslinker: a versatile platform for Cys-peptide–hydrazine conjugation and interplay

Abstract

In this work, we describe the preparation of a heterobifunctional 2-formylphenylboronic acid (2-FPBA)–maleimide crosslinker and explore its versatility in the preparation of various bioconjugates. We demonstrate the straightforward attachment of hydrazine payloads to cysteine residues in peptides, as well as the crosslinking of different thiol-bearing peptides or payloads with N-terminal cysteine peptides. Importantly, the dynamic nature of the 2-FPBA handle enables an interplay between the thiazolidine and diazaborine forms, which allows obtaining various products controlled by (and in some cases independent of) the order of addition of the components.

Graphical abstract: A 2-formylphenylboronic acid (2FPBA)-maleimide crosslinker: a versatile platform for Cys-peptide–hydrazine conjugation and interplay

Associated articles

Supplementary files

Article information

Article type
Communication
Submitted
10 Mot 2021
Accepted
15 Jan 2021
First published
15 Jan 2021

Org. Biomol. Chem., 2021,19, 6221-6226

A 2-formylphenylboronic acid (2FPBA)-maleimide crosslinker: a versatile platform for Cys-peptide–hydrazine conjugation and interplay

J. P. M. António, H. Faustino and P. M. P. Gois, Org. Biomol. Chem., 2021, 19, 6221 DOI: 10.1039/D1OB00917F

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