591-57-1

Basic information

• Product Name: (2R)-2-hydroxy-3-oxopropyl dihydrogen phosphate
• Synonyms: (2R)-2-Hydroxy-3-oxopropyl dihydrogen phosphate; propanal, 2-hydroxy-3-(phosphonooxy)-, (2R)-
• CAS NO: 591-57-1
• Molecular Formula: C₃H₇O₆P
• Molecular Weight: 170.0578
• Mol File: 591-57-1.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 399.2°C at 760 mmHg
• Flash Point: 195.2°C
• Density: 1.721g/cm³
• Vapor Pressure: 4.94E-08mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: (2R)-2-hydroxy-3-oxopropyl dihydrogen phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-hydroxy-3-oxopropyl dihydrogen phosphate(591-57-1)
• EPA Substance Registry System: (2R)-2-hydroxy-3-oxopropyl dihydrogen phosphate(591-57-1)

Safety Data

• Hazardous Substances Data: 591-57-1(Hazardous Substances Data)

Usage

General Description

(2R)-2-hydroxy-3-oxopropyl dihydrogen phosphate is a chemical compound with the molecular formula C3H7O6P. It is a phosphorylated metabolite that plays a crucial role in the glycolytic pathway. Specifically, it acts as an intermediate in the conversion of 3-phosphoglycerate to 2-phosphoglycerate, a key step in the generation of ATP through glycolysis. (2R)-2-hydroxy-3-oxopropyl dihydrogen phosphate is important for energy production in cells and is involved in various metabolic processes. It is also a fundamental component in the synthesis of nucleotides and lipids. Overall, (2R)-2-hydroxy-3-oxopropyl dihydrogen phosphate is a vital molecule with diverse functions in cellular metabolism.

Upstream product

• 7685-50-9 2-deoxy-D-ribose 5-phosphate 
• 488-69-7 fructose-1,6-bisphosphate 
• 13137-52-5 D-arabinose-5-phosphate 
• 765-34-4 Glycidaldehyde 
• 57-04-5 dihydroxyacetone phosphate 
• 102783-56-2 dihydroxyacetone 3-phosphate dilithium salt 
• 4220-97-7 phosphoric acid mono-(2,3-dihydroxy-3-indol-3-yl-propyl ester) 
• 57-03-4 lysophosphatidic acid 
• 585-18-2 D-erythrose 4-phosphate 
• 34693-15-7 fructose 1,6-diphosphate 
• 643-13-0 D-fructose-6-phosphate 
• 84446-94-6 2-O-glycoloyl-D-glyceraldehyde 3-phosphate 
• 4212-65-1 D-xylulose 5-phosphate 
• 27244-54-8 3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate 

Downstream Products

• 820-11-1 D-(-)-3-phosphoglyceric acid 
• 4212-65-1 D-xylulose 5-phosphate 
• 643-13-0 D-fructose-6-phosphate 
• 141258-86-8 (2-13C₁)-D-Fructose 1,6-bisphosphate 
• 453-17-8 D-Glyceraldehyde 
• 20283-52-7 D-glyceraldehyde 3-phosphate 
• 7685-50-9 2-deoxy-D-ribose 5-phosphate 
• 16434-11-0 2-deoxy-D-ribose 5-phosphate, free acid 
• 56-82-6 Glyceraldehyde 
• 38168-82-0 1,3-Biphospho-D-glyceric acid 
• 1107-69-3 pyruvaldehyde bis-(2,4-dinitro-phenylhydrazone) 
• 86119-84-8 phosphoric acid 
• 78-98-8 2-oxopropanal 
• 312-85-6 sodium lactate 

Relevant articles and documents

Chemical and enzymatic methodologies for the synthesis of enantiomerically pure glyceraldehyde 3-phosphates

Glyceraldehyde 3-phosphates are important intermediates of many central metabolic pathways in a large number of living organisms. d-Glyceraldehyde 3-phosphate (d-GAP) is a key intermediate during glycolysis and can as well be found in a variety of other metabolic pathways. The opposite enantiomer, l-glyceraldehyde 3-phosphate (l-GAP), has been found in a few exciting new pathways. Here, improved syntheses of enantiomerically pure glyceraldehyde 3-phosphates are reported. While d-GAP was synthesized by periodate cleavage of d-fructose 6-phosphate, l-GAP was obtained by enzymatic phosphorylation of l-glyceraldehyde. 1H- and 31P NMR spectroscopy was applied in order to examine pH-dependent behavior of GAP over time and to identify potential degradation products. It was found that GAP is stable in acidic aqueous solution below pH 4. At pH 7, methylglyoxal is formed, whereas under alkaline conditions, the formation of lactic acid could be observed.

N-sulfonyl hydroxamate derivatives as inhibitors of class II fructose-1,6-diphosphate aldolase

Dihydroxyacetone-phosphate and phosphonate derivatives were synthesized bearing a N-sulfonyl hydroxamate moiety. The phosphate derivatives represent competitive inhibitors for the class II-FBP aldolase catalyzed reaction, while the phosphonate isosteres are comparatively weaker inhibitors.

Prebiotic synthesis of aminooxazoline-5′-phosphates in water by oxidative phosphorylation

RNA is essential to all life on Earth and is the leading candidate for the first biopolymer of life. Aminooxazolines have recently emerged as key prebiotic ribonucleotide precursors, and here we develop a novel strategy for aminooxazoline-5′-phosphate synthesis in water from prebiotic feedstocks. Oxidation of acrolein delivers glycidaldehyde (90%), which directs a regioselective phosphorylation in water and specifically affords 5′-phosphorylated nucleotide precursors in upto 36% yield. We also demonstrated a generational link between proteinogenic amino acids (Met, Glu, Gln) and nucleotide synthesis.

Dual Activity of Quinolinate Synthase: Triose Phosphate Isomerase and Dehydration Activities Play Together to Form Quinolinate

Quinolinate synthase (NadA) is an Fe4S4 cluster-containing dehydrating enzyme involved in the synthesis of quinolinic acid (QA), the universal precursor of the essential coenzyme nicotinamide adenine dinucleotide. The reaction catalyzed by NadA is not well understood, and two mechanisms have been proposed in the literature that differ in the nature of the molecule (DHAP or G-3P) that condenses with iminoaspartate (IA) to form QA. In this article, using biochemical approaches, we demonstrate that DHAP is the triose that condenses with IA to form QA. The capacity of NadA to use G-3P is due to its previously unknown triose phosphate isomerase activity.