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Issue 41, 2013
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Conformations of d-xylose: the pivotal role of the intramolecular hydrogen-bonding

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Abstract

Crystalline samples of D-xylose have been vaporized by laser ablation and probed in the gas phase using Fourier transform microwave spectroscopy. The rotational spectrum revealed the existence of two α-D-xylopyranose conformers stabilized by the anomeric effect and cooperative hydrogen bond networks. The experiment spectroscopically tracked fine structural changes upon clockwise and counterclockwise arrangements of the OH groups in the observed conformers. The five monosubstituted 13C species of the most abundant conformer cc-α-4C1 have also been observed in their natural abundance, and its structure has been derived. This work demonstrates the pivotal role that the intramolecular hydrogen-bonding network plays in the conformational behavior of free monosaccharides.

Graphical abstract: Conformations of d-xylose: the pivotal role of the intramolecular hydrogen-bonding

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Article information


Submitted
05 Jun 2013
Accepted
15 Aug 2013
First published
16 Aug 2013

Phys. Chem. Chem. Phys., 2013,15, 18243-18248
Article type
Paper

Conformations of D-xylose: the pivotal role of the intramolecular hydrogen-bonding

I. Peña, S. Mata, A. Martín, C. Cabezas, A. M. Daly and J. L. Alonso, Phys. Chem. Chem. Phys., 2013, 15, 18243
DOI: 10.1039/C3CP52345D

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