Conformational analysis of the disaccharide methyl α-D-mannopyranosyl-(1→3)-2-O-acetyl-β-D-mannopyranoside monohydrate

Author:

Zhang Wenhui,Wu Qingquan,Oliver Allen G.,Serianni Anthony S.

Abstract

The crystal structure of methyl α-D-mannopyranosyl-(1→3)-2-O-acetyl-β-D-mannopyranoside monohydrate, C15H26O12·H2O, (II), has been determined and the structural parameters for its constituent α-D-mannopyranosyl residue compared with those for methyl α-D-mannopyranoside. Mono-O-acetylation appears to promote the crystallization of (II), inferred from the difficulty in crystallizing methyl α-D-mannopyranosyl-(1→3)-β-D-mannopyranoside despite repeated attempts. The conformational properties of the O-acetyl side chain in (II) are similar to those observed in recent studies of peracetylated mannose-containing oligosaccharides, having a preferred geometry in which the C2—H2 bond eclipses the C=O bond of the acetyl group. The C2—O2 bond in (II) elongates by ∼0.02 Å upon O-acetylation. The phi (φ) and psi (ψ) torsion angles that dictate the conformation of the internal O-glycosidic linkage in (II) are similar to those determined recently in aqueous solution by NMR spectroscopy for unacetylated (II) using the statistical program MA′AT, with a greater disparity found for ψ (Δ = ∼16°) than for φ (Δ = ∼6°).

Funder

National Science Foundation

Publisher

International Union of Crystallography (IUCr)

Subject

Materials Chemistry,Inorganic Chemistry,Physical and Theoretical Chemistry,Condensed Matter Physics

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Structural properties of D-mannopyranosyl rings containing O-acetyl side-chains;Acta Crystallographica Section C Structural Chemistry;2019-07-29

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