D-Mannoheptulose , CAS:3615-44-9

D-MannoheptuloseD-Glucose is phosphorylated by glucokinase and three tissue-specific hexokinases to produce glucose-6-phosphate in humans. D-Mannoheptulose is a heptose that inhibits glucokinases and hexokinases from diverse organisms through competition with D-glucose (Ki = 0.25 mM). It blocks glucose oxidation and glucose-mediated insulin release from pancreatic islet cells. D-Mannoheptulose prevents the conversion of glucose to glucose-6-phosphate that can mediate the activation of the carbohydrate response element binding protein. By blocking glucose phosphorylation, D-mannoheptulose causes transient hyperglycemia in dogs when given at 1 g/kg but not at 8 mg/kg, although postprandial energy expenditure is increased at the lower dose.Title:?D-manno-HeptuloseCAS Registry Number:?3615-44-9Additional Names:?D-manno-KetoheptoseMolecular Formula:?C7H14O7Molecular Weight:?210.18Percent Composition:?C 40.00%, H 6.71%, O 53.29%Literature References:?Isoln from the wet pulp of the fruit of the avocado tree,?Persea gratissima?Gaertn. f. (P. americana?Mill.),?Lauraceae:?LaForge,?J. Biol. Chem.?28,?511 (1917); Montgomery, Hudson,?J. Am. Chem. Soc.?61,?1654 (1939); Richtmyer in?Methods in Carbohydrate Chemistry?R. L. Whistler?et al.,?Eds.?vol. 1,?173 (1962).Properties:?Large, transparent prisms from methanol, mp 151-152?. [a]D20?+29? (c = 2 in H2O). Sol in water. Usually accompanied by perseitol. Although perseitol is much more insol in water and methanol than?D-manno-heptulose, clean separation of the two substances is not always easy and may require patient fractional crystn.Melting point:?mp 151-152?Optical Rotation:?[a]D20?+29? (c = 2 in H2O)CAS Number3615-44-9Product NameD-MannoheptuloseIUPAC Name(3S,4S,5R,6R)-1,3,4,5,6,7-hexahydroxyheptan-2-oneMolecular FormulaC7H14O7Molecular Weight210.18 g/molInChIInChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5-,6-,7+/m1/s1InChI KeyHSNZZMHEPUFJNZ-QMTIVRBISA-NSMILESC(C(C(C(C(C(=O)CO)O)O)O)O)OSynonymsD-Manno-2-heptulose; (+)-Mannoheptulose; NSC 226836;Canonical SMILESC(C(C(C(C(C(=O)CO)O)O)O)O)OIsomeric SMILESC([C@H]([C@H]([C@@H]([C@@H](C(=O)CO)O)O)O)O)OCAS No: 3615-44-9,654-29-5 Synonyms: D-Manno-2-heptulose MDL No: MFCD00037814 Chemical Formula: C7H14O7 Molecular Weight: 210.182References: 1. Rasschaert J, Kadiata MM, Malaisse WJ, Mol. Cell. Biochem. 2001, Oct, 226(1-2), 77-812. Ramirez R, Rasschaert J, Laghmich A, Louchami K, Nadi AB, Jijakli H, Kadiata MM, Sener A, Malaisse WJ, Int. J. Mol. Med. 2001, Jun, 7(6), 631-8