title: Modifications in the nitric acid oxidation of D-mannose: X-ray crystal structure of N,N'-dimethyl D-mannaramide.
abstract: Nitric acid oxidation of D-mannose was carried out under an oxygen atmosphere using a computer controlled reactor. The process represents a catalytic oxidation of D-mannose with oxygen as the terminal oxidant. The crude oxidation product was esterified with methanolic HCl and the esterified product directly converted to crystalline N,N'-dimethyl-D-mannaramide with methylamine. Treatment of the diamide in aqueous sodium hydroxide gave solid disodium D-mannarate. The X-ray crystal structure of N,N'-dimethyl-D-mannaramide was determined as a model for the repeating D-mannaramide units of stereoregular poly(alkylene-D-mannaramides). Disodium D-mannarate was prepared as a precursor of esterified D-mannaric acid for use as a reactive diacid monomer to prepare poly-D-mannaramides.
authors.affiliation: Shafizadeh Rocky Mountain Center for Wood and Carbohydrate Chemistry, The University of Montana, Missoula, MT 59812, USA. ccarpenter01@ugf.edu
authors.forename: Chrissie A
authors.initials: CA
authors.lastname: Carpenter
authors.forename: Kenneth I
authors.initials: KI
authors.lastname: Hardcastle
authors.forename: Donald E
authors.initials: DE
authors.lastname: Kiely
mesh_terms: D018360:Crystallography, X-Ray; D008358:Mannose / Q000031:analogs & derivatives* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D017942:Nitric Acid / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: C000592594:N,N'-dimethyl D-mannaramide; D017942:Nitric Acid; D008358:Mannose