Mannoheptulose

D-Mannoheptulose
Names
IUPAC name
D-Manno-hept-2-ulose
Identifiers
3615-44-9 Yes
ChemSpider 12080 Yes
Jmol-3D images Image
PubChem 12600
Properties
Molecular formula
C7H14O7
Molar mass 210.18 g·mol−1
Density 1.7 g cm−3
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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.

References

  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).