Crystal structure and solid-state 13C NMR analysis of N-o-, N-m- and N-p-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamines, and their N-acetyl derivatives.
The X-ray diffraction analysis of N-o-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine (1), N-m-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamines, N-p-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamines, and their N-acetyl derivatives was performed. The sugar moieties always adopt (4)C1 conformations, however, due to crystal packing forces they are always slightly distorted. It was found that except N-acetyl, N-m-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine (5), none of the glucopyranosylamines studied in this paper form strong hydrogen bonds in the crystal lattice. Additionally, (5) crystallizes with a molecule of water, which occupies a special crystallographic position (on the twofold axis) and links two sugar molecules by hydrogen bonds. The CP MAS NMR spectra confirmed the presence of the intermolecular hydrogen bond involving the molecule of water in (5). Moreover, it was proved that in (1) an intramolecular hydrogen bond is formed between the glycosidic linkage and the nitro group.
Temeriusz
Andrzej
A
Department of Chemistry, Warsaw University, Pasteura 1, 02-093 Warszawa, Poland. atemer@chem.uw.edu.pl
Gubica
Tomasz
T
Rogowska
Paulina
P
Paradowska
Katarzyna
K
Cyrański
Michał K
MK
D000107:Acetylation; D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular
C014124:4-nitrophenyl-N-acetyl-2-deoxyglucopyranoside; D000117:Acetylglucosamine