Reversible covalent interactions of β-aminoboronic acids with carbohydrate derivatives. Issue 11 (20th January 2017)

• Record Type: Journal Article
• Authors: Garrett, Graham E.; Diaz, Diego B.; Yudin, Andrei K.; Taylor, Mark S.
• Is Part Of: Chemical communications. Volume 53:Issue 11(2017)
• Page Start: 1809
• Page End: 1812
• Publication Date: 2017-01-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc09640a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : β-Aminoalkylboronic acids bind reversibly to diol groups, a phenomenon that can be exploited in carbohydrate recognition and in catalysis. 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.