Structural Expression of Exo-Anomeric Effect

The Journal of Physical Chemistry Letters
Elena R AlonsoJose L Alonso

Abstract

Structural signatures for exo-anomeric effect have been extracted from the archetypal methyl-β-D-xyloside using broadband Fourier transform microwave spectroscopy combined with laser ablation. Spectrum analysis allows the determination of a set of rotational constants, which has been unequivocally attributed to conformer cc-β-(4)C1 g-, corresponding to the global minimum of the potential energy surface, where the aglycon residue (CH3) orientation contributes to maximization of the exo-anomeric effect. Further analysis allowed the determination of the rs structure, based on the detection of 11 isotopologues--derived from the presence of six (13)C and five (18)O atoms--observed in their natural abundances. The observed glycosidic C1-O1 bond length decrease (1.38 Å) can be interpreted in terms of the exo-anomeric effect. As such, the exo-anomeric effect presents itself as one of the main driving forces controlling the shape of many biologically important oligosaccharides.

References

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Feb 13, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Celina BermúdezJosé L Alonso
Sep 26, 2013·Physical Chemistry Chemical Physics : PCCP·Isabel PeñaJosé L Alonso
Oct 10, 2013·Angewandte Chemie·Isabel PeñaJosé L Alonso
Oct 15, 2013·Chemical Communications : Chem Comm·Carlos CabezasJosé L Alonso
Feb 28, 2015·Topics in Current Chemistry·José L Alonso, Juan C López
May 27, 2015·Chemical Communications : Chem Comm·Isabel PeñaJosé L Alonso

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Citations

Apr 27, 2017·Physical Chemistry Chemical Physics : PCCP·Ander CamiruagaJosé A Fernández
Jul 26, 2017·Journal of Chemical Theory and Computation·Daniele LicariVincenzo Barone
Jul 18, 2017·Molecular BioSystems·Ander CamiruagaJosé A Fernández
Aug 27, 2019·Angewandte Chemie·Iker LeónJose Luis Alonso
May 6, 2020·Physical Chemistry Chemical Physics : PCCP·I LeónJ L Alonso
Aug 23, 2017·Scientific Reports·Alexey G GerbstNikolay E Nifantiev
Jan 29, 2021·The Journal of Physical Chemistry Letters·Aran InsaustiEmilio J Cocinero
Jun 2, 2021·Angewandte Chemie·Elena R AlonsoJose Luis Alonso
Dec 8, 2017·The Journal of Physical Chemistry. a·Vanessa CortijoJosé L Alonso

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