Mannoheptulose

D-Mannoheptulose
Names
	IUPAC name D-Manno-hept-2-ulose
Identifiers
CAS Number	3615-44-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	12080 ;
ECHA InfoCard	100.020.723
PubChem CID	12600;
CompTox Dashboard (EPA)	DTXSID60879012 ;
	InChI 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 Key: HSNZZMHEPUFJNZ-QMTIVRBISA-N ; 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;
	SMILES O=C([C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)CO;
Properties
Chemical formula	C7H14O7
Molar mass	210.182 g·mol−1
Density	1.7 g cm−3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Mannoheptulose is a hexokinase inhibitor. It is a heptose, a monosaccharide with seven carbon atoms. By blocking the enzyme hexokinase, it prevents glucose phosphorylation. As a result, the breakdown of glucose is inhibited. It is found as D-mannoheptulose in avocados.^[1]

Mannoheptulose has been reported to inhibit insulin secretion from pancreas.^[2] This inhibition occurs because when mannoheptulose is present the glycolysis is inhibited (because there is no production of glucose-6-P) therefore no increase in ATP concentration which is required to close the KATP channel in the beta cells of the pancreas causing a diminution of calcium entry and insulin secretion.

Because of its inhibition of glycolysis in vitro, it has been investigated as a novel nutraceuticals for weight management for dogs.^[3]^[4] However, while mannoheptulose is suggested to affect the energy balance of adult dogs, independent of dosage and physical activity, research disagrees whether it significantly alters energy expenditure in dogs.

References

^ Dai, N; Schaffer, A; Petreikov, M; Shahak, Y; Giller, Y; Ratner, K; Levine, A; Granot, D (1999). "Overexpression of Arabidopsis hexokinase in tomato plants inhibits growth, reduces photosynthesis, and induces rapid senescence". The Plant cell. 11 (7): 1253–66. doi:10.1105/tpc.11.7.1253. PMC 144264. PMID 10402427.
^ Lucke, Christoph; Kagan, Avir; Adelman, Neil; Glick, Seymour (1972). "Effect of 2-Deoxy-D-Glucose and Mannoheptulose on the Insulin Response to Amino Acids in Rabbits". Diabetes. 21 (1): 1–5. doi:10.2337/diab.21.1.1.
^ McKnight, Leslie; Root-McCraig, Jared; Wright, David; Davenport, Gary; France, James; Shoveller, Anna Kate (2015). "Dietary Mannoheptulose Does Not Significantly Alter Daily Energy Expenditure in Adult Labrador Retrievers". PLos One. 10 (12): e0143324. doi:10.1371/journal.pone.0143324.{{cite journal}}: CS1 maint: unflagged free DOI (link)
^ McKnight, Leslie; Eyre, Ryan; Gooding, Margaret; Davenport, Gary; Shoveller, Anna Kate (2015). "Dietary Mannoheptulose Increases Fasting Serum Glucagon Like Peptide-1 and Post-Prandial Serum Ghrelin Concentrations in Adult Beagle Dogs". Animals. 5 (2): 442–454. doi:10.3390/ani5020365.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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[1] Dai, N; Schaffer, A; Petreikov, M; Shahak, Y; Giller, Y; Ratner, K; Levine, A; Granot, D (1999). "Overexpression of Arabidopsis hexokinase in tomato plants inhibits growth, reduces photosynthesis, and induces rapid senescence". The Plant cell. 11 (7): 1253–66. doi:10.1105/tpc.11.7.1253. PMC 144264. PMID 10402427.

[2] Lucke, Christoph; Kagan, Avir; Adelman, Neil; Glick, Seymour (1972). "Effect of 2-Deoxy-D-Glucose and Mannoheptulose on the Insulin Response to Amino Acids in Rabbits". Diabetes. 21 (1): 1–5. doi:10.2337/diab.21.1.1.

[dog1-3] McKnight, Leslie; Root-McCraig, Jared; Wright, David; Davenport, Gary; France, James; Shoveller, Anna Kate (2015). "Dietary Mannoheptulose Does Not Significantly Alter Daily Energy Expenditure in Adult Labrador Retrievers". PLos One. 10 (12): e0143324. doi:10.1371/journal.pone.0143324.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[dog2-4] McKnight, Leslie; Eyre, Ryan; Gooding, Margaret; Davenport, Gary; Shoveller, Anna Kate (2015). "Dietary Mannoheptulose Increases Fasting Serum Glucagon Like Peptide-1 and Post-Prandial Serum Ghrelin Concentrations in Adult Beagle Dogs". Animals. 5 (2): 442–454. doi:10.3390/ani5020365.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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