title: Solubility and crystal structure of N-(1-deoxy-beta-D-fructopyranos-1-yl)-l-histidine monohydrate ('D-fructose-l-histidine').
abstract: Within a set of food-related Amadori compounds, crystalline N-(1-deoxy-beta-D-fructopyranos-1-yl)-l-histidine monohydrate (Fru-l-HisxH(2)O) has an unusually low solubility in water, which we determined as 0.21 g/100 g at 25 degrees C. The majority of the other fructose-amino acid conjugates have solubilities exceeding 100 g/100 g in water at this temperature. We report the crystal structure data on Fru-l-HisxH(2)O. The conformation of the carbohydrate is the normal (2)C(5) pyranose chair. Bond lengths and valence angles compare well with the average values from a number of pyranose structures. All hydroxyl and carboxyl oxygen atoms, all nitrogen atoms and the water molecule are involved in an extensive hydrogen bonding, which forms a network of infinite chains with small antidromic rings.
authors.affiliation: Department of Biochemistry, University of Missouri, Columbia, MO 65211, USA. MossineV@missouri.edu <MossineV@missouri.edu>
authors.forename: Valeri V
authors.initials: VV
authors.lastname: Mossine
authors.forename: Charles L
authors.initials: CL
authors.lastname: Barnes
authors.forename: Thomas P
authors.initials: TP
authors.lastname: Mawhinney
mesh_terms: D002236:Carbohydrate Conformation; D003460:Crystallization; D003461:Crystallography; D018360:Crystallography, X-Ray; D005632:Fructose / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D006639:Histidine / Q000737:chemistry*; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D012995:Solubility
chemical_list: D005632:Fructose; C033188:fructosyl-glycine; D006639:Histidine; D005998:Glycine