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CAS 79082-92-1

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Fructose 2,6-diphosphate

Description:
Fructose 2,6-diphosphate (F2,6BP) is a crucial regulatory metabolite in carbohydrate metabolism, particularly in glycolysis and gluconeogenesis. It is a bisphosphate derivative of fructose and plays a significant role in the regulation of key enzymes such as phosphofructokinase-1 (PFK-1) and fructose-1,6-bisphosphatase. F2,6BP is synthesized from fructose-6-phosphate by the enzyme phosphofructokinase-2 (PFK-2) and can be hydrolyzed back to fructose-6-phosphate by fructose-2,6-bisphosphatase. This compound is characterized by its ability to enhance the affinity of PFK-1 for its substrate, thus promoting glycolysis when energy is needed. Conversely, it inhibits fructose-1,6-bisphosphatase, reducing gluconeogenesis. F2,6BP levels are tightly regulated by hormonal signals, particularly insulin and glucagon, reflecting the metabolic state of the cell. Its role as a signaling molecule highlights its importance in maintaining glucose homeostasis and energy balance in various tissues, especially in the liver and muscle.
Formula:C6H14O12P2
InChI:InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1
InChI key:InChIKey=YXWOAJXNVLXPMU-ZXXMMSQZSA-N
SMILES:O(P(=O)(O)O)[C@@]1(CO)[C@@H](O)[C@H](O)[C@@H](COP(=O)(O)O)O1
Synonyms:
  • D-Fructose 2,6-diphosphate
  • Fructose 2,6-bisphosphate
  • Fructose 2,6-diphosphate
  • β-D-Fructose 2,6-diphosphate
  • β-D-Fructofuranose, 2,6-bis(dihydrogen phosphate)
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