27244-54-8

Basic information

• Product Name: 4,5-dihydroxy-2-oxo-6-phosphonooxy-hexanoic acid
• Synonyms: 2-Keto-3-deoxy-6-phosphogluconic acid;4,5-dihydroxy-2-oxo-6-phosphonooxy-hexanoic acid;2-Keto-3-deoxy-6-phosphogluconate;2-Keto-2,3-dideoxy-6-O-phosphono-D-gluconic acid;3-Deoxy-D-erythro-2-hexulosonic acid 6-phosphoric acid;KDPG;(4S,5R)-4,5-Dihydroxy-2-oxo-6-phosphonooxyhexanoic acid lithium salt;2-Dehydro-3-deoxy-6-phospho-D-gluconate lithium salt
• CAS NO: 27244-54-8
• Molecular Formula: C₆H₁₁O₉P
• Molecular Weight: 258.12
• Mol File: 27244-54-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 614.2°Cat760mmHg
• Flash Point: 325.3°C
• Appearance: /
• Density: 1.835g/cm³
• Vapor Pressure: 1.18E-17mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: -20°C
• CAS DataBase Reference: 4,5-dihydroxy-2-oxo-6-phosphonooxy-hexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-dihydroxy-2-oxo-6-phosphonooxy-hexanoic acid(27244-54-8)
• EPA Substance Registry System: 4,5-dihydroxy-2-oxo-6-phosphonooxy-hexanoic acid(27244-54-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 27244-54-8(Hazardous Substances Data)

Usage

Definition

ChEBI: The 5-phospho derivative of 2-dehydro-D-gluconic acid.

InChI:InChI=1/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/t3-,5+/m0/s1

Upstream product

• 591-57-1 D-glyceraldehyde-3-phosphate 
• 127-17-3 2-oxo-propionic acid 

Downstream Products

• 591-57-1 D-glyceraldehyde-3-phosphate 
• 127-17-3 2-oxo-propionic acid 

Relevant articles and documents

Microbial synthesis of 3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate

A microbial route was explored for the synthesis of 3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate (2-keto-3-deoxy-6-phosphogluconate, KDPG). Two strains of bacteria, Alcaligenes eutrophus H16 F34 (DSM 529) and Escherichia coli DF 71 (CGSC 4880), lacking in KDPG-aldolase activity were tested for excretion of KDPG. Using pyruvate and gluconate as carbon sources, Alcaligenes eutrophus H16 F34 accumulated and excreted 3-deoxy-D-erythro-hexulosonic acid 6-phosphate into the culture broth, while the E. coli strain, using pyruvate and glucuronate, failed. KDPG was isolated from the culture supernatant of Alcaligenes eutrophus H16 F34 in 78% yield and 5 g scale with respect to the consumed gluconate. A microbial route was explored for the synthesis of 3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate (2-keto-3-deoxy-6-phosphogluconate, KDPG). Two strains of bacteria, Alcaligenes eutrophus H16 F34 (DSM 529) and Escherichia coli DF 71 (CGSC 4880), lacking in KDPG-aldolase activity were tested for excretion of KDPG. Using pyruvate and gluconate as carbon sources, Alcaligenes eutrophus H16 F34 accumulated and excreted 3-deoxy-D-erythro-hexulosonic acid 6-phosphate into the culture broth, while the E. coli strain, using pyruvate and glucuronate, failed. KDPG was isolated from the culture supernatant of Alcaligenes eutrophus H16 F34 in 78% yield and 5 g scale with respect to the consumed gluconate.