Molecular and crystal structures of N-arylglycopyranosylamines formed by reaction between sulfanilamide and D-ribose, D-arabinose and D-mannose.
The X-ray crystal structures of three monosaccharide derivatives prepared by the reaction of sulfanilamide with D-ribose, D-arabinose, and D-mannose have been determined. The derivatives are N-(p-sulfamoylphenyl)-alpha-D-ribopyranosylamine (1), N-(p-sulfamoylphenyl)-alpha-D-arabinopyranosylamine (2), and N-(p-sulfamoylphenyl)-beta-D-mannopyranosylamine monohydrate (3). The monosaccharide ring of 1 and 2 has the 1C4 conformation, stabilized in 1 by an intramolecular hydrogen bond from 0-2 to 0-4. Compound 3 has the 4C1 conformation at the monosaccharide ring and the gt conformation at the C-6-O-6 side chain. Occupancy of the water molecule in the crystal of 3 actually examined was 22%. The degree of interaction between sulfamoyl groups and monosaccharide moieties varies from structure to structure. The packing arrangement of 2 involves hydrogen bonding between sulfamoyl groups and monosaccharide hydroxyl groups, but interactions of this type are fewer in 1, and in 3 the hydrogen bonds are either strictly between monosaccharide hydroxyl groups or strictly between sulfamoyl groups. Pairs of hydrogen bonds (two-point contacts) link neighboring molecules in all three structures, between screw-axially related molecules in 1 and 2 and between translationally related molecules in 3. The contact in 3 defined by the O-3-H...O-5 and O-6-H...O-4 hydrogen bonds is found in several other N-aryl-beta-D-mannopyranosylamine crystal structures and is apparently an especially favorable mode of intermolecular interaction in these compounds.
Ojala
C R
CR
Department of Chemistry, Normandale Community College, Bloomington, MN 55431, USA. whojala@stthomas.edu
Ostman
J M
JM
Ojala
W H
WH
Hanson
S E
SE
D000606:Amino Sugars / Q000737:chemistry*; D001089:Arabinose / Q000737:chemistry; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008358:Mannose / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D012266:Ribose / Q000737:chemistry; D000077145:Sulfanilamide; D013424:Sulfanilamides / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D000606:Amino Sugars; D009005:Monosaccharides; D013424:Sulfanilamides; D014867:Water; D000077145:Sulfanilamide; D012266:Ribose; D001089:Arabinose; D008358:Mannose