4429-47-4

Basic information

• Product Name: 2,5-ANHYDRO-D-GLUCITOL-1,6-DIPHOSPHATE
• Synonyms: 2,5-ANHYDRO-D-GLUCITOL-1,6-DIPHOSPHATE;2,5-anhydro-D-glucitol 1,6-Bis(dihydrogen phosphate)
• CAS NO: 4429-47-4
• Molecular Formula: C6H14O11P2
• Molecular Weight: 324.12
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Inhibitors
• Mol File: 4429-47-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 2,5-ANHYDRO-D-GLUCITOL-1,6-DIPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-ANHYDRO-D-GLUCITOL-1,6-DIPHOSPHATE(4429-47-4)
• EPA Substance Registry System: 2,5-ANHYDRO-D-GLUCITOL-1,6-DIPHOSPHATE(4429-47-4)

Safety Data

• Hazardous Substances Data: 4429-47-4(Hazardous Substances Data)

Usage

Uses

An effective competitive inhibitor of phosphofructokinase (EC 2.7.1.11)

Upstream product

• 300807-58-3 ((2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol 
• 287733-95-3 (2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 
• 27826-73-9 2,5-anhydro-D-glucitol 
• 162239-10-3 1-deoxy-1-β-ethenyl-2,3,5-tri-O-benzyl-L-xylose 
• 300807-67-4 C₃₀H₃₀O₁₁P₂ 

Relevant articles and documents

Synthesis of Selectively Labeled D-Fructose and D-Fructose Phosphate Analogues Locked in the Cyclic Furanose Form

2,5-Anhydroglucitol and 2,5-anhydromannitol and their 6-phosphate and 1,6-diphosphate derivatives are cyclic analogues of the α and β anomers of D-fructofuranose, D-fructofuranose-6-phosphate, and D-fructofuranose-1,6-diphosphate. They were synthesized from protected D-mannose or D-glucose. The synthetic method was developed with emphasis on selective 2H labeling of these compounds, as a model for 3H incorporation, which will be used for further biochemical studies. A key cyclization step, based on a benzyl ether nucleophilic attack on an activated alcohol, constructed the ring system. The stereochemistry at C2 (α/β anomers) and at C5 (D sugar) was controlled by selective epimerizations. Mono- and diphosphate analogues were obtained from the same intermediate by changing the sequence of deprotection and phosphorylation steps.