2627-73-8

Basic information

• Product Name: 3-deoxy-D-arabino-heptulosonate-7-phosphate
• Synonyms: 3-deoxy-D-arabino-heptulosonate-7-phosphate
• CAS NO: 2627-73-8
• Molecular Formula: C₇H₁₃O₁₀P
• Molecular Weight: 288.145881
• Mol File: 2627-73-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 674.7°Cat760mmHg
• Flash Point: 361.8°C
• Appearance: /
• Density: 1.859g/cm³
• Vapor Pressure: 4.25E-21mmHg at 25°C
• Refractive Index: 1.589
• PKA: 1.84±0.10(Predicted)
• CAS DataBase Reference: 3-deoxy-D-arabino-heptulosonate-7-phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-deoxy-D-arabino-heptulosonate-7-phosphate(2627-73-8)
• EPA Substance Registry System: 3-deoxy-D-arabino-heptulosonate-7-phosphate(2627-73-8)

Safety Data

• Hazardous Substances Data: 2627-73-8(Hazardous Substances Data)

Usage

Uses

3-Deoxy-D-arabino-heptulosonate 7-Phosphate is an intermediate useful in the synthesis of 3-Deoxy-D-arabinoheptulosonic Acid 7-Phosphate Disodium Salt (D232050), which stands at the beginning of the enzyme-catalyzed cascade that starts with this seven-carbon carbohydrate and ends with the aromatic amino acids phenylalanine, tyrosine, and tryptophan.

InChI:InChI=1/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)

Upstream product

• 4265-07-0 phospho(enol)pyruvic acid mono potassium salt 
• 103302-15-4 sodium D-erythrose 4-phosphate 

Downstream Products

• 10534-44-8 3-dehydroquinic acid 

Relevant articles and documents

A thermodynamic study of the reactions: {2-dehydro-3-deoxy-D-arabino-heptanoate 7-phosphate(aq) = 3-dehydroquinate(aq) + phosphate(aq)} and {3-dehydroquinate(aq) = 3-dehydroshikimate(aq) + H2O(l)}

Microcalorimetry and high-performance liquid chromatography (h.p.l.c.) have been used to conduct a thermodynamic investigation of reactions catalyzed by 3-dehydroquinate synthase and by 3-dehydroquinate dehydratase. These are the second and third reactions in the metabolic pathway leading to the formation of chorismate. The two reactions are: {DAHP(aq) = 3-dehydroquinate(aq) + phosphate(aq)} and {3-dehydroquinate(aq) = 3-dehydroshikimate(aq) + H2O(l)}. The h.p.l.c. measurements showed that the first reaction proceeded to completion and that the value of the apparent equilibrium constant for the second reaction was K′ = (4.6 ± 1.5) (Hepes buffer, temperature T = 298.15 K, pH = 7.50, and ionic strength Im = 0.065 mol·kg-1). Calorimetric measurements led to a molar enthalpy of reaction ΔrHm (cal) = -(50.9 ± 1.1) kJ·mol-1 (Hepes buffer, T = 298.15 K, pH = 7.46, Im = 0.070 mol·kg-1) for the first reaction and to ΔrHm (cal) = (2.3 ± 2.3) kJ·mol-1 (Hepes buffer, T = 298.15 K, pH = 7.42, Im = 0.069 mol·kg-1) for the second reaction. These results were analyzed in terms of a chemical equilibrium model that accounts for the multiplicity of ionic states of the reactants and products. These calculations gave thermodynamic quantities at T = 298.15 K and Im = 0 for chemical reference reactions involving specific ionic forms. For the reaction DAHP3-(aq) = 3-dehydroquinate-(aq) + HPO42-(aq), the standard molar enthalpy of reaction ΔrHmo = -(51.1 ± 4.5) kJ·mol-1. For the reaction 3-de-hydroquinate(aq) = (3-dehydroshikimate(aq) + H2O(l), the equilibrium constant K = (4.6 ± 1.5) and ΔrHmo = (2.3 ± 2.3) kJ·mol-1. A Benson type approach was used to estimate the standard molar entropy change ΔrSmo for the first reference reaction and led to the value K ≈ 2·1014 for this reaction. Values of the apparent equilibrium constants and the standard transformed Gibbs free energy changes ΔrGmo under approximately physiological conditions are given for the biochemical reactions.