Conformational flexibility around the Gal-β-(1 → 3)-Glc linkage: Experimental evidence for the existence of the anti-ψ conformation in aqueous solution

Paloma Vidal; Jesús Jiménez-Barbero; Juan F Espinosa

doi:10.1016/j.carres.2016.06.009

Conformational flexibility around the Gal-β-(1 → 3)-Glc linkage: Experimental evidence for the existence of the anti-ψ conformation in aqueous solution

Carbohydr Res. 2016 Oct 4:433:36-40. doi: 10.1016/j.carres.2016.06.009. Epub 2016 Jul 5.

Authors

Paloma Vidal¹, Jesús Jiménez-Barbero², Juan F Espinosa³

Affiliations

¹ Discovery Chemistry Research and Technologies, Centro de Investigación Lilly, Avenida de la Industria 30, 28108 Alcobendas, Madrid, Spain.
² Centro de Investigaciones Biológicas, Ramiro de Maeztu 9, 28040 Madrid, Spain. Electronic address: [email protected].
³ Discovery Chemistry Research and Technologies, Centro de Investigación Lilly, Avenida de la Industria 30, 28108 Alcobendas, Madrid, Spain. Electronic address: [email protected].

PMID: 27434833
DOI: 10.1016/j.carres.2016.06.009

Abstract

NOE-based analysis of the disaccharide β-Gal-(1 → 3)-β-Glc-OMe (1), especially a diagnostic Gal1-Glc4 NOE detected in a HSQC-NOESY spectrum, reveals the existence of the anti-ψ conformer in aqueous solution in addition to the major syn conformer. This result provides experimental proof of conformational flexibility around the aglyconic bond of β-(1 → 3) disaccharides, in contrast to previous studies that suggested that the flexibility around this linkage was restricted to the syn conformational region.

Keywords: Anti conformation; Conformational analysis; Disaccharide flexibility; Molecular modeling; NMR.

MeSH terms

Carbohydrate Conformation
Disaccharides / chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular

Substances

Disaccharides