Fast Diazaborine Formation of Semicarbazide Enables Facile Labeling of Bacterial Pathogens.

ABSTRACT: Bioorthogonal conjugation chemistry has enabled the development of tools for the interrogation of complex biological systems. Although a number of bioorthogonal reactions have been documented in literature, they are less ideal for one or several reasons including slow kinetics, low stability of the conjugated product, requirement of toxic catalysts, and side reactions with unintended biomolecules. Herein we report a fast (>10³ M^-1 s^-1) and bioorthogonal conjugation reaction that joins semicarbazide to an aryl ketone or aldehyde with an ortho-boronic acid substituent. The boronic acid moiety greatly accelerates the initial formation of a semicarbazone conjugate, which rearranges into a stable diazaborine. The diazaborine formation can be performed in blood s

SUBMITTER: Bandyopadhyay A 

PROVIDER: S-EPMC6191850 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature