An inhibitor of glucokinases and hexokinases
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Isomer(s)
46208D-glycero-D-galacto-Heptose
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D-Mannoheptulose

Item No. 16548

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 1 mg/mlPBS (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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $54

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    10 mg

    $102

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    25 mg

    $238

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    50 mg

    $418

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    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).1,2,3 It blocks glucose oxidation and glucose-mediated insulin release from pancreatic islet cells.4,5 D-Mannoheptulose prevents the conversion of glucose to glucose-6-phosphate that can mediate the activation of the carbohydrate response element binding protein.6 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.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Coore, H.G., and Randle, P.J. Inhibition of glucose phosphorylation by mannoheptulose. Biochem. J. 91(1), 56-59 (1964).

    2. Ashcroft, S.J.H., and Randle, P.J. Enzymes of glucose metabolism in normal mouse pancreatic islets. Biochem. J. 119(1), 5-15 (1970).

    3. Dai, N., Schaffer, A., Petreikov, M., et al. Overexpression of Arabidopsis hexokinase in tomato plants inhibits growth, reduces photosynthesis, and induces rapid senescence. Plant Cell 11(7), 1253-1266 (1999).

    4. Ashcroft, S.J.H., Weerasinghe, L.C., and Randle, P.J. Interrelationship of islet metabolism, adenosine triphosphate content and insulin release. Biochem. J. 132(2), 223-231 (1973).

    5. Johnson, D., Shepherd, R.M., Gill, D., et al. Glucose-dependent modulation of insulin secretion and intracellular calcium ions by GKA50, a glucokinase activator. Diabetes 56(6), 1694-1702 (2007).

    6. Li, M.V., Chen, W., Harmancey, R.N., et al. Glucose-6-phosphate mediates activation of the carbohydrate responsive binding protein (ChREBP). Biochem. Biophys. Res. Commun. 395(3), 395-400 (2010).

    7. McKnight, L.L., Flickinger, E.A., France, J., et al. Mannoheptulose has differential effects on fasting and postprandial energy expenditure and respiratory quotient in adult Beagle dogs fed diets of different macronutrient contents. J. Nutr. Sci. 3, e17 (2014).

    Product Citations

    Wang, A., Huen, S.C., Luan, H.H., et al. Opposing effects of fasting metabolism on tissue tolerance in bacterial and viral inflammation. Cell 166(6), 1512-1525 (2016).