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Pantoic acid

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Pantoic acid
Names
Preferred IUPAC name (2R)-2,4-Dihydroxy-3,3-dimethylbutanoic acid
Other names D-Pantoic acid; D-Pantoate; B(R)-2,4-dihydroxy-3,3-dimethylbutanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H12O4/c1-6(2,3-7)4(8)5(9)10/h4,7-8H,3H2,1-2H3,(H,9,10)/t4-/m0/s1Key: OTOIIPJYVQJATP-BYPYZUCNSA-N
SMILES
  • O=C(O)(O)C(C)(C)CO
Properties
Chemical formula C6H12O4
Molar mass 148.158 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Pantoic acid is the alpha hydroxy acid with the formula HOCH2C(CH3)2CH(OH)CO2H. The compound is almost always encountered in a biological context, as an aqueous solution of its conjugate base pantoate HOCH2C(CH3)2CH(OH)CO2-. The amide of pantoic acid with β-alanine is pantothenic acid (vitamin B5), a component of coenzyme A.

Biosynthesis

Its biosynthesis proceeds from ketoisovalerate by hydroxymethylation:

(CH3)2CHC(O)CO2 + CH2O → HOCH2(CH3)2CC(O)CO2

This conversion is catalyzed by ketopantoate hydroxymethyltransferase, which gives ketopantoate. Ketopantoate is reduced by ketopantoate reductase to pantoate, using NADH as the hydride source.

The amide derived from pantoic acid and GABA is the pharmaceutical drug hopantenic acid.

References

  1. Pantoic acid, Merriam Webster Medical Dictionary
  2. Begley, Tadhg P.; Kinsland, Cynthia; Strauss, Erick (2001). "The Biosynthesis of Coenzyme a in Bacteria". Cofactor Biosynthesis. Vitamins & Hormones. Vol. 61. pp. 157–171. doi:10.1016/S0083-6729(01)61005-7. ISBN 9780127098616. PMID 11153265.

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