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Glyceric acid

From Wikipedia, the free encyclopedia
Glyceric acid[1]
Names
Preferred IUPAC name
2,3-Dihydroxypropanoic acid
Other names
Glyceric acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.006.795Edit this at Wikidata
UNII
  • InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7) ☒N
    Key: RBNPOMFGQQGHHO-UHFFFAOYSA-N ☒N
  • InChI=1/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)
    Key: RBNPOMFGQQGHHO-UHFFFAOYAE
  • C(C(C(=O)O)O)O
Properties
C3H6O4
Molar mass106.08 g/mol
Appearancecolorless syrup
Melting point<25 °C
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Glyceric acid refers toorganic compounds with the formulaHOCH2CH(OH)CO2H. It occurs naturally and is classified as three-carbonsugar acid. It ischiral.Salts andesters of glyceric acid are known asglycerates.

Production

[edit]

Glyceric acid is usually produced by oxidation ofglycerol. A typical oxidant isnitric acid, but catalytic oxidations have been developed also:[2][3]

HOCH2CH(OH)CH2OH + O2 → HOCH2CH(OH)CO2H + H2O

As glycerol isprochiral, the oxidation of the two terminal alcohol groups gives distinct enantiomers of glyceric acid. Oxidation of both primary alcohols givestartronic acid:

HOCH2CH(OH)CH2OH + 2 O2 → HO2CCH(OH)CO2H + 2 H2O

Biochemistry

[edit]

Severalphosphate derivatives of glyceric acid, including2-phosphoglyceric acid,3-phosphoglyceric acid,2,3-bisphosphoglyceric acid, and1,3-bisphosphoglyceric acid, are intermediates inglycolysis.[4] 3-Phosphoglyceric acid is an intermediate in the biosynthesis of theamino acidserine, which in turn can be used in the synthesis ofglycine andcysteine.[5]

Glyceric acid occurs naturally inPopulus tremula andArdisia crenata.[6]

References

[edit]
  1. ^Merck Index, 11th Edition,4378.
  2. ^Habe, Hiroshi; Fukuoka, Tokuma; Kitamoto, Dai; Sakaki, Keiji (2009). "Biotechnological production of d-glyceric acid and its application".Applied Microbiology and Biotechnology.84 (3):445–452.doi:10.1007/s00253-009-2124-3.PMID 19621222.S2CID 9144557.
  3. ^Yang, Lihua; Li, Xuewen; Chen, Ping; Hou, Zhaoyin (2019)."Selective oxidation of glycerol in a base-free aqueous solution: A short review".Chinese Journal of Catalysis.40 (7):1020–1034.doi:10.1016/S1872-2067(19)63301-2.S2CID 196894235.
  4. ^Reece, Jane B. (2009).Biology (8th ed.). San Francisco, CA: Pearson. pp. 168–169.ISBN 978-0-8053-6844-4.
  5. ^J. Berg, J. L. Tymoczko, L. Stryer.Biochemistry, 7th Edition.{{cite book}}: CS1 maint: multiple names: authors list (link)
  6. ^PubChem."Glyceric acid".pubchem.ncbi.nlm.nih.gov. Retrieved2023-01-12.
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