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
CAS Number	1112-33-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	388387;
PubChem CID	439251;
UNII	0J1TL6G6J9 ;
CompTox Dashboard (EPA)	DTXSID70861968 DTXSID90963716, DTXSID70861968 ;
	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/s1 Key: OTOIIPJYVQJATP-BYPYZUCNSA-N;
	SMILES O=C(O)[C@H](O)C(C)(C)CO;
Properties
Chemical formula	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). Infobox references

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

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

^ Pantoic acid, Merriam Webster Medical Dictionary
^ 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.

External links

Media related to Pantoic acid at Wikimedia Commons

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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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