1981-49-3

Basic information

• Product Name: (2-hydroxy-3-phosphonooxy-propanoyl)oxyphosphonic acid
• Synonyms: (2-hydroxy-3-phosphonooxy-propanoyl)oxyphosphonic acid;Glyceric acid 1,3-biphosphate;glycerate 1,3-biphosphate;(2R)-2-Hydroxy-1,3-bis(phosphonooxy)-1-propanone;1,3-Bisphosphoglycerate;1,3-Diphoshoglycerate;1,3-Diphosphoglycerate;3-O-Phosphono-D-glyceric 1-phosphoric anhydride
• CAS NO: 1981-49-3
• Molecular Formula: C₃H₈O₁₀P₂
• Molecular Weight: 266.04
• Mol File: 1981-49-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 638.7°Cat760mmHg
• Flash Point: 340°C
• Appearance: /
• Density: 2.143g/cm³
• Vapor Pressure: 5.32E-19mmHg at 25°C
• Refractive Index: 1.572
• PKA: 1.36±0.10(Predicted)
• CAS DataBase Reference: (2-hydroxy-3-phosphonooxy-propanoyl)oxyphosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2-hydroxy-3-phosphonooxy-propanoyl)oxyphosphonic acid(1981-49-3)
• EPA Substance Registry System: (2-hydroxy-3-phosphonooxy-propanoyl)oxyphosphonic acid(1981-49-3)

Safety Data

• Hazardous Substances Data: 1981-49-3(Hazardous Substances Data)

Usage

Uses

Phosphono 2-hydroxy-3- phosphonooxypropanoate is a biological metabolite of glucose and can be involved in oncogenesis.

InChI:InChI=1/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)

Upstream product

• 591-57-1 D-glyceraldehyde-3-phosphate 
• 820-11-1 3-phosphoglyceric acid 
• 86-01-1 Guanosine 5'-triphosphate 
• 2564-35-4 2'-deoxyguanosine 5'-triphosphate 
• 56-65-5 ATP 
• 1927-31-7 dATP 
• 63-39-8 UTP 
• 365-08-2 dTTP 
• 65-47-4 cytidine triphosphate 
• 13191-15-6 β-L-CTP 
• 66341-18-2 Acyclovir triphosphate 
• 68726-28-3 2',3'-dideoxyguanosine-5'-triphosphate 
• 24027-80-3 2',3'-dideoxyadenosine 5'-triphosphate 
• 142-10-9 DL-glyceraldehyde 3-phosphate 

Downstream Products

• 820-11-1 3-phosphoglyceric acid 
• 56-65-5 ATP 

Relevant articles and documents

Kinetic and mechanistic characterization of the glyceraldehyde 3-phosphate dehydrogenase from Mycobacterium tuberculosis

Glyceraldehyde 3-phosphate dehydrogenase (GAPDH) is a glycolytic protein responsible for the conversion of glyceraldehyde 3-phosphate (G3P), inorganic phosphate and nicotinamide adenine dinucleotide (NAD+) to 1,3-bisphosphoglycerate (1,3-BPG) and the reduced form of nicotinamide adenine dinucleotide (NADH). Here we report the characterization of GAPDH from Mycobacterium tuberculosis (Mtb). This enzyme exhibits a kinetic mechanism in which first NAD+, then G3P bind to the active site resulting in the formation of a covalently bound thiohemiacetal intermediate. After oxidation of the thiohemiacetal and subsequent nucleotide exchange (NADH off, NAD+ on), the binding of inorganic phosphate and phosphorolysis yields the product 1,3-BPG. Mutagenesis and iodoacetamide (IAM) inactivation studies reveal the conserved C158 to be responsible for nucleophilic catalysis and that the conserved H185 to act as a catalytic base. Primary, solvent and multiple kinetic isotope effects revealed that the first half-reaction is rate limiting and utilizes a step-wise mechanism for thiohemiacetal oxidation via a transient alkoxide to promote hydride transfer and thioester formation.