A 2-formylphenylboronic acid (2FPBA)-maleimide crosslinker: a versatile platform for Cys-peptide–hydrazine conjugation and interplay
João P. M. António, Hélio Faustino, Pedro M. P. Góis
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.
Topics & Concepts
MaleimideChemistryThiazolidineCysteineHydrazine (antidepressant)PeptideCombinatorial chemistryThiolAmino acidOrganic chemistryBiochemistryEnzymeChemical Synthesis and AnalysisPeptidase Inhibition and AnalysisClick Chemistry and Applications