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Molecules 2015, 20(2), 2892-2902; doi:10.3390/molecules20022892

Synthesis and Molecular Structure of the 5-Methoxycarbonylpentyl α-Glycoside of the Upstream, Terminal Moiety of the O-Specific Polysaccharide of Vibrio cholerae O1, Serotype Inaba

1
NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA
2
Department of Chemistry, Western Kentucky University, 1906 College Heights Blvd., Bowling Green, KY 42101-1709, USA
3
Southern Regional Research Center, US Department of Agriculture, 1100 Robert E Lee Blvd, New Orleans, LA 70124, USA
*
Author to whom correspondence should be addressed.
Academic Editors: Marco Terreni and Caterina Temporini
Received: 14 January 2015 / Accepted: 5 February 2015 / Published: 11 February 2015
(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)
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Abstract

The trimethylsilyl trifluoromethanesulfonate (TMSOTf)-catalyzed reaction of methyl 6-hydroxyhexanoate with 3-O-benzyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-levulinoyl-α-d-mannopyranosyl trichloroacetimidate followed by a two-step deprotection (hydrogenolysis over Pd/C catalyst and Zemplén deacylation, to simultaneously remove the acetyl and levulinoyl groups) gave 5-(methoxycarbonyl)pentyl 4-(3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranoside. The structure of the latter, for which crystals were obtained in the analytically pure state for the first time, followed from its NMR and high-resolution mass spectra and was confirmed by X-ray crystallography. The molecule has two approximately linear components; a line through the aglycon intersects a line through the mannosyl and tetronylamido groups at 120°. The crystal packing separates the aglycon groups from the tetronylamido and mannosyl groups, with only C-H…O hydrogen bonding among the aglycon groups and N-H…O, O-H…O and C-H…O links among the tetronylamido and mannosyl groups. A carbonyl oxygen atom accepts the strongest O-H…O hydrogen bond and two strong C-H…O hydrogen bonds. The geometric properties were compared with those of related molecules. View Full-Text
Keywords: Vibrio cholerae O1; glycosylation; glycosidation; crystal structure Vibrio cholerae O1; glycosylation; glycosidation; crystal structure
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Xu, P.; Stevens, E.D.; French, A.D.; Kováč, P. Synthesis and Molecular Structure of the 5-Methoxycarbonylpentyl α-Glycoside of the Upstream, Terminal Moiety of the O-Specific Polysaccharide of Vibrio cholerae O1, Serotype Inaba. Molecules 2015, 20, 2892-2902.

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