Issue 18, 2020

Design, synthesis and structure of a frustrated benzoxaborole and its applications in the complexation of amines, amino acids, and protein modification

Abstract

This study describes the design and synthesis of arylboronic acid 2, the first example of a permanently open “frustrated” benzoxaborole, along with an exploration of its application in bioconjugation. An efficient and high yielding seven-step synthesis was optimized. NMR experiments confirmed that compound 2 exists in the open ortho-hydroxyalkyl arylboronic acid structure 2-I, a form that is effectively prevented to undergo a dehydrative cyclization as a result of unfavorable geometry. Compound 2-I conjugates effectively with amines to form stable hemiaminal ether structures, including a highly effective reaction with lysozyme. Complexation with cysteine induces an open structure containing a free hydroxymethyl arm, with the amino and thiol groups reacting preferentially with the formyl group to form a N,S-acetal.

Graphical abstract: Design, synthesis and structure of a frustrated benzoxaborole and its applications in the complexation of amines, amino acids, and protein modification

Supplementary files

Article information

Article type
Paper
Submitted
18 Meur. 2020
Accepted
20 Ebr. 2020
First published
21 Ebr. 2020

Org. Biomol. Chem., 2020,18, 3492-3500

Design, synthesis and structure of a frustrated benzoxaborole and its applications in the complexation of amines, amino acids, and protein modification

J. Bhangu, R. M. Whittal and D. G. Hall, Org. Biomol. Chem., 2020, 18, 3492 DOI: 10.1039/D0OB00572J

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