| Disorder and conformational analysis of methyl β-D-galactopyranosyl-(1→4)-β-D-xylopyranoside. | |
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MedLine Citation:
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PMID: 22223286 Owner: NLM Status: In-Data-Review |
Abstract/OtherAbstract:
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Methyl β-D-galactopyranosyl-(1→4)-β-D-xylopyranoside, C(12)H(22)O(10), (II), crystallizes as colorless needles from water with positional disorder in the xylopyranosyl (Xyl) ring and no water molecules in the unit cell. The internal glycosidic linkage conformation in (II) is characterized by a ϕ' torsion angle (C2'(Gal)-C1'(Gal)-O1'(Gal)-C4(Xyl)) of 156.4 (5)° and a ψ' torsion angle (C1'(Gal)-O1'(Gal)-C4(Xyl)-C3(Xyl)) of 94.0 (11)°, where the ring atom numbering conforms to the convention in which C1 denotes the anomeric C atom, and C5 and C6 denote the hydroxymethyl (-CH(2)OH) C atoms in the β-Xyl and β-Gal residues, respectively. By comparison, the internal linkage conformation in the crystal structure of the structurally related disaccharide, methyl β-lactoside [methyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside], (III) [Stenutz, Shang & Serianni (1999). Acta Cryst. C55, 1719-1721], is characterized by ϕ' = 153.8 (2)° and ψ' = 78.4 (2)°. A comparison of β-(1→4)-linked disaccharides shows considerable variability in both ϕ' and ψ', with the range in the latter (∼38°) greater than that in the former (∼28°). Inter-residue hydrogen bonding is observed between atoms O3(Xyl) and O5'(Gal) in the crystal structure of (II), analogous to the inter-residue hydrogen bond detected between atoms O3(Glc) and O5'(Gal) in (III). The exocyclic hydroxymethyl conformations in the Gal residues of (II) and (III) are identical (gauche-trans conformer). |
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Authors:
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Wenhui Zhang; Allen G Oliver; Anthony S Serianni |
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Publication Detail:
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Type: Journal Article Date: 2011-12-06 |
Journal Detail:
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Title: Acta crystallographica. Section C, Crystal structure communications Volume: 68 ISSN: 1600-5759 ISO Abbreviation: Acta Crystallogr C Publication Date: 2012 Jan |
Date Detail:
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Created Date: 2012-01-06 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 8305826 Medline TA: Acta Crystallogr C Country: United States |
Other Details:
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Languages: eng Pagination: o7-o11 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670, USA. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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