Pyrocinchonimides Conjugate to Amine Groups on Proteins via Imide Transfer.

ABSTRACT: Advances in bioconjugation, the ability to link biomolecules to each other, small molecules, surfaces, and more, can spur the development of advanced materials and therapeutics. We have discovered that pyrocinchonimide, the dimethylated analogue of maleimide, undergoes a surprising transformation with biomolecules. The reaction targets amines and involves an imide transfer, which has not been previously reported for bioconjugation purposes. Despite their similarity to maleimides, pyrocinchonimides do not react with free thiols. Though both lysine residues and the N-termini of proteins can receive the transferred imide, the reaction also exhibits a marked preference for certain amines that cannot solely be ascribed to solvent accessibility. This property is peculiar among amine-targe

SUBMITTER: Richardson MB 

PROVIDER: S-EPMC7337330 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature