D-Mannoheptulose

D-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.Formal Name: D-manno-2-heptulose. CAS Number: 3615-44-9. Synonyms: NSC 226836. Molecular Formula: C7H14O7. Formula Weight: 210.2. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 mg/ml, DMSO: 20 mg/ml, Ethanol: 1 mg/ml, PBS (pH 7.2): 10 mg/ml. SMILES: OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(CO)=O. InChi Code: InChI=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/s1. InChi Key: HSNZZMHEPUFJNZ-QMTIVRBISA-N.