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Crystal structures of methyl 6-O-n-alkanoyl-β-d-glucopyranosides

✍ Scribed by Yutaka Abe; Kazuaki Harata; Masami Fujiwara; Kazuo Ohbu

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
397 KB
Volume
269
Category
Article
ISSN
0008-6215

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✦ Synopsis

The crystal structures of methyl 6-O-n-octanoyl-/3-D-glucopyranoside 1 and methyl 6-O-n-decanoyl-/3-D-glucopyranoside 2, which are types of glycosurfactants, were determined by X-ray analysis. Anhydrous crystals were obtained from a diethyl ether-acetone solution. The crystals are monoclinic, and the space group is P21 with Z = 2. The cell dimensions are as follows: 1, a = 7.760(1), b = 7.373(1), c = 15.514(1) /~ fl = 102.91(1)°; 2, a = 7.724(1), b = 7.351(1), c = 16.957(2) ~, /3 = 94.81(1) °. The glucopyranoside moieties are in a 4C 1 chair conformation and the conformation of the alkyl chain is the all-trans type. The molecules are arranged parallel to the a-c plane in a bilayer structure where alkyl chains are interdigitated. The sugar moieties are stacked to form a hydrophilic zone elongated parallel to the ab plane and arranged with a packing structure similar to that of methyl /3-D-glucopyranoside in spite of a substituted long alkyl chain. Hydrogen bondings of sugar moieties are found only between the bilayers.

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