Work

A Bioorthogonal Reaction of N ‐Oxide and Boron Reagents

Year: 2015

Type: article

Abstract: The development of bioorthogonal reactions has classically focused on bond-forming ligation reactions. In this report, we seek to expand the functional repertoire of such transformations by introducing a new bond-cleaving reaction between N-oxide and boron reagents. The reaction features a large dynamic range of reactivity, showcasing second-order rate constants as high as 2.3×10(3) M(-1) s(-1) using diboron reaction partners. Diboron reagents display minimal cell toxicity at millimolar concentrations, penetrate cell membranes, and effectively reduce N-oxides inside mammalian cells. This new bioorthogonal process based on miniscule components is thus well-suited for activating molecules within cells under chemical control. Furthermore, we demonstrate that the metabolic diversity of nature enables the use of naturally occurring functional groups that display inherent biocompatibility alongside abiotic components for organism-specific applications.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201508861

Authors: Justin Kim, Carolyn R. Bertozzi

Institutions: Howard Hughes Medical Institute, Stanford University

Language: English

Topic: Click Chemistry and Applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Howard Hughes Medical Institute, Adolph C. and Mary Sprague Miller Institute for Basic Research in Science, University of California Berkeley, National Institute of General Medical Sciences

Awards: G1134119878, Metabolic Engineering with Bioorthogonal Chemical Reporters, Chemical glycobiology tool development: Proximity-based modalities