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Sulfoaminoglucitols: synthesis of 2-amino-2,3 (and 2,6)-dideoxy-d-glucitol-3 (and 6)-sulfonic acids and X-ray crystal structure of the monohydrate of the 6-sulfo derivative

✍ Scribed by JoséG. Fernández-Bolaños; Salud García; José Fernández-Bolaños; María Jesús Diánez; María Dolores Estrada; Amparo López-Castro; Simeón Pérez

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
526 KB
Volume
282
Category
Article
ISSN
0008-6215

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✦ Synopsis

2-Amino-2,3-dideoxy-D-glucitol-3-sulfonic acid (3) and 2-amino-2,6-dideoxy-o-glucitol-6sulfonic acid (4) were prepared by reduction of 2-amino-2,3 (and 2,6)-dideoxy-D-glucopyranose-3 (and 6)-sulfonic acids with sodium borohydride. The crystal structure of 4 monohydrate (C6H15NOTS.H20) is orthorhombic, space group P212121 with unit cell dimensions a= 8.289(2), b = 24.548(5), and c = 5.149(2) A. A planar zig-zag conformation is observed in which N-2 and 0-4 atoms are aligned 1,3-parallel, stabilized by an intramolecular hydrogen bond (N-H.-. 0-4). The sulfo and the amino group form a zwitterion and two conformations are found for the ammonium group.

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