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Chem Commun (Camb). 2017 Feb 07;53(11):1809-1812. doi: 10.1039/c6cc09640a. Epub 2017 Jan 20.

Reversible covalent interactions of β-aminoboronic acids with carbohydrate derivatives.

Chemical communications (Cambridge, England)

Graham E Garrett, Diego B Diaz, Andrei K Yudin, Mark S Taylor

Affiliations

  1. Department of Chemistry, University of Toronto, Toronto, ON M5S 3H6, Canada. [email protected] [email protected].

PMID: 28106188 DOI: 10.1039/c6cc09640a

Abstract

β-Aminoalkylboronic acids are capable of binding to carbohydrate derivatives through reversible covalent interactions. An anthracene-bearing β-aminoboronic acid has been synthesized, enabling determinations of association constants for binding of sugars by fluorescence spectroscopy. The diol-binding properties of β-aminoboronic acids are also useful in catalysis: one such compound displays remarkably high activity for regioselective O-acylation of a pyranoside derivative.

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