The X-ray crystal structures of the glycosaminoglycan-related monosaccharides 2-deoxy-2-(sulfoamino)-a-o-glucopyranose sodium salt dihydrate, 2-amino-2-deoxy-a,fl-o-glucopyranose 3-(hydrogen sulfate) monohydrate, and 2-amino-2-deoxy-ot-D-glucopyranose 6-(hydrogen sulfate) monohydrate have been deter
Structural studies of O-sulfated D-glucosamines. The crystal and molecular structures of 2-amino-2-deoxy-α/ β-D-glucopyranose 3-sulfate (free acid) and 2-amino-2-deoxy-β-D-glucopyranose 6-sulfate (free base)
✍ Scribed by William Mackie; Edwin A. Yates; Doriano Lamba
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 473 KB
- Volume
- 266
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
The crystal and molecular structures of 2-amino-2-deoxy-a/fl-D-glucopyranose 3-sulfate (1) and 2-amino-2-deoxy-fl-D-glucopyranose 6-sulfate (2) have been determined by direct methods. The sugar rings have the expected 4C1 conformation and the geometries of the sulfate groups are comparable with those found in previous investigations except for a significant shortening of the C--O bond and closing of the C-<)-S bond angle in 2.
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The crystal structure of a-D-Manp-(1 +3)-/?-D-Manp-( 1-+4)-a-D-GlcNAcp has been determined by the direct method using the multi-solution, tangentzformula, and "magic integer" procedures. The space group is P2,, and 2 molecules are in the unit cell with c1 = 9.894 ( 5), b = 10.372 (6), c = 11.816 (6)
The reaction of 2-amino-2-deoxy-D-glucose hydrochloride with 5,5-dimethyl-2-phenylaminomethylene-1 ,fcyclohexanedione in MeOH in the presence of Et,N afforded 2-deoxy-2-[(4,4-dimethyl-2,6-dioxocyclohexylidenemethyl)amino]-~-~ucase (6) in yields >75%. Glycosidation of 6 with different alcohols (MeOH,
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