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Combined 1H, 13C and 11B NMR and mass spectral assignments of boronate complexes of D-(+)-glucose, D-(+)-mannose, methyl-α-D-glucopyranoside, methyl-β-D-galactopyranoside and methyl-α-D-mannopyranoside

✍ Scribed by Reem Smoum; Abraham Rubinstein; Morris Srebnik

Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 120 KB
Volume: 41
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1301

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✦ Synopsis

Abstract

Complex formation between N‐butylboronic acid and D‐(+)‐glucose, D‐(+)‐mannose, methyl‐α‐D‐glucopyranoside, methyl‐β‐D‐galactopyranoside and methyl α‐D‐mannopyranoside under neutral conditions was investigated by ^1^H, ^13^C and ^11^B NMR spectroscopy and gas chromatography–mass spectrometry (GC–MS) D‐(+)‐Glucose and D‐(+)‐mannose formed complexes where the boronates are attached to the 1,2:4,6‐ and 2,3:5,6‐positions of the furanose forms, respectively. On the other hand, the boronic acid binds to the 4,6‐positions of the two methyl derivatives of glucose and galactose. Methyl α‐D‐mannopyranoside binds two boronates at the 2,3:4,6‐positions. ^11^B NMR was used to show the ring size of the complexed sugars and the boronate. GC–MS confirmed the assignments. Copyright © 2003 John Wiley & Sons, Ltd.

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