Pantoic acid

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
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C6H12O4/c1-6(2,3-7)4(8)5(9)10/h4,7-8H,3H2,1-2H3,(H,9,10)/t4-/m0/s1
    Key: OTOIIPJYVQJATP-BYPYZUCNSA-N
  • O=C(O)[C@H](O)C(C)(C)CO
Properties
C6H12O4
Molar mass 148.158 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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),[1] a component of coenzyme A.

Biosynthesis

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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.[2]

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

References

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  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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