Octanoic Hydrazide-Linked Chitooligosaccharides-2,5-Anhydro-d-Mannofuranose
نویسنده
چکیده
Chitooligosaccharide with one 2,5-anhydro-D-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous acid depolymerization of chitosan. The reducing-end functionalization of COSamf by reductive amination with octanoic hydrazide in the presence of NaBH3CN was achieved in high yield. The chemical structure of the targeted octanoic hydrazide-linked COSamf was fully characterized by NMR spectroscopy and MALDI-TOF mass spectrometry. This synthesis opens the way to a new generation of COSamf derivatives with potential amphiphilic properties.
منابع مشابه
Chitooligosaccharide-2,5-anhydro-D-mannonic Acid
Chitooligosaccharide with one 2,5-anhydro-D-mannofuranose unit at the reducing end (COSamf) was prepared by nitrous deamination of fully N-deacetylated chitosan. The oxidation of the amf-unit by chlorite sodium was achieved in high yield. The chemical structure of the targeted chitooligosaccharide-2,5-anhydro-D-mannonic acid with a degree of polymerization ~10 was fully characterized by NMR spe...
متن کاملNovel and facile synthesis of furanodictines A and B based on transformation of 2-acetamido-2-deoxy-D-glucose into 3,6-anhydro hexofuranoses.
A novel synthesis of furanodictines A [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-glucofuranose (1)] and B [2-acetamido-3,6-anhydro-2-deoxy-5-O-isovaleryl-D-mannofuranose (2)] is described starting from 2-acetamido-2-deoxy-D-glucose (GlcNAc). The synthetic protocol is based on deriving the epimeric bicyclic 3,6-anhydro sugars [2-acetamido-3,6-anhydro-2-deoxy-D-glucofuranose (4) and 2-acet...
متن کاملThe substrate and anomeric specificity of fructokinase.
Fructokinase from beef liver is shown to be specific for the /3-furanose anomer of D-fructose (and the LY anomer of Lsorbose) by showing that certain 2,5-anhydroalditols are substrates, while other 2,5-anhydro compounds, 2,6-anhydro-D-mannitol, and 2,6-anhydro-D-glucitol are not. Km and Ir,,, values relative to D-fructose at pH 7.5, 25”, 4 mu MgATP are 2,5-anhydro-D-mannitol (1.7 mu, 1.97); 2,5...
متن کاملInhibition of gluconeogenesis and glycogenolysis by 2,5-anhydro-D-mannitol.
2,5-Anhydro-D-mannitol (100 to 200 mg/kg) decreased blood glucose by 17 to 58% in fasting mice, rats, streptozotocin-diabetic mice, and genetically diabetic db/db mice. Serum lactate in rats was elevated 56% by 2,5-anhydro-D-mannitol, but this could be prevented by dichloroacetate (200 mg/kg) or thiamin (200 mg/kg). In hepatocytes from fasted rats, 1 mM 2,5-anhydro-D-mannitol inhibited gluconeo...
متن کاملInhibition of bovine hepatic fructose-1,6-diphosphatase by substrate analogs.
Purified bovine hepatic fructose-1,6-diphosphatase, which exhibits maximal activity at neutral pH, is competitively inhibited by several analogs of its substrate, fructose 1,6-diphosphate. These include glucose 1,6-diphosphate (Ki = 9.4 X 10(-5) M), hexitol 1,6-diphosphate (Ki = 2.3 X 10(-4) M), and 2,5-anhydro-D-mannitol 1,6-diphosphate (Ki = 3.3 X 10(-8) M), and 2,5-anhydro-D-glucitol 1,6-dip...
متن کامل