Фосфогидроксипировиноградная кислота

Description

Phosphohydroxypyruvic acid is 2-oxo-3-(phosphonooxo)propanoic acid, a phosphorylated derivative of hydroxypyruvic acid. Known in biochemistry as 3-phosphohydroxypyruvate (3-PHP), it is an intermediate in the phosphorylated L-serine biosynthesis pathway. The product item relates to biochemical reagents and standards for metabolomics.

Basic Attributes

• CAS No.: 3913-50-6
• Chemical Formula: C3H5O7P
• Exact weight: 184.04
• Molecular weight according to the supplier's card: 527.63
• UNII: ZX4PWG857L
• HS code: 2931900090
• PSA: 210.39000
• XLogP3: 5.10370

The value of 527.63 does not agree with the given formula C3H5O7P, which corresponds to a mass of 184.04 - it coincides with the specified exact mass. Both values ​​are left as they are given in the original product card; When ordering, the mass should be specified with the supplier along with the form of delivery (acid or salt).

Physical properties

• Appearance: solid
• Density: 2.119 g/cm³
• Boiling point: 497.8 °C at 760 mm Hg. Art.
• Flash point: 254.9 °C
• Refractive index: 1.581
• Storage conditions: −20 °C

Biochemical role

The compound is the second link in the phosphorylated serine biosynthesis pathway, which branches off from glycolysis:

• 3-phosphoglycerate is oxidized by phosphoglycerate dehydrogenase (PHGDH) with the participation of NAD to 3-phosphohydroxypyruvate - this is the rate-limiting step of the pathway
• phosphoserine aminotransferase (PSAT1) transfers an amino group from glutamate to 3-phosphohydroxypyruvate, forming 3-phosphoserine and α-ketoglutarate
• phosphoserine phosphatase (PSPH) cleaves off phosphate, yielding L-serine

In tumor cells, about 10% of 3-phosphoglycerate is removed through this pathway, and PHGDH activity serves as a target in the development of inhibitors of serine metabolism. Hence the practical interest in the connection.

Scope of application

• substrate and standard for the study of enzymes of the serine pathway - PHGDH, PSAT1, PSPH
• reference substance in metabolomic analysis by LC-MS methods
• reagent for work on tumor cell metabolism and screening of PHGDH inhibitors

Safety Information

• Transport codes: UN 2811, class 6.1, packing group III
• Hazard class code: 21/22 - harmful in contact with skin and if swallowed
• Safety instructions: 36/37 - wear suitable protective clothing and gloves
• Tags: Xn
• WGK Germany: 3

Storage

Freeze storage at −20 °C, container tightly closed. Phosphorylated metabolites are hydrolytically labile, so solutions are prepared immediately before the experiment and stored in frozen aliquots.