Ketopantoic acid

Ketopantoic acid
Names
	Other names 4-Hydroxy-3,3-dimethyl-2-oxobutanoic acid; 2-Dehydropantoic acid
Identifiers
CAS Number	470-30-4;
3D model (JSmol)	Interactive image;
Beilstein Reference	2242422
ChEBI	CHEBI:17094;
ChemSpider	37;
DrugBank	DB03795;
KEGG	C00966;
PubChem CID	38;
CompTox Dashboard (EPA)	DTXSID90274258 ;
	InChI InChI=1S/C6H10O4/c1-6(2,3-7)4(8)5(9)10/h7H,3H2,1-2H3,(H,9,10) Key: PKVVTUWHANFMQC-UHFFFAOYSA-N;
	SMILES CC(C)(CO)C(=O)C(=O)O;
Properties
Chemical formula	C6H10O4
Molar mass	146.142 g·mol−1
Appearance	colorless or white
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Ketopantoic acid is the organic compound with the formula HOCH₂(CH₃)₂CC(O)CO₂H. At physiological conditions, ketopantoic acid exists as its conjugate base, ketopantoate (HOCH₂(CH₃)₂CC(O)CO₂⁻).

Biosynthetic context

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 substrate for 2-dehydropantoate 2-reductase,[1] which produces pantoate, a precursor to pantothenic acid, a common prosthetic group.[2]

References

Matak-Vinković, Dijana; Vinković, Mladen; Saldanha, S. Adrian; Ashurst, Jennifer L.; von Delft, Frank; Inoue, Tsuyoshi; Miguel, Ricardo Nunez; Smith, Alison G.; Blundell, Tom L.; Abell, Chris (2001). "Crystal Structure of Escherichia coli Ketopantoate Reductase at 1.7 Å Resolution and Insight into the Enzyme Mechanism". Biochemistry. 40 (48): 14493–14500. doi:10.1021/bi011020w. PMID 11724562.
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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[1] Matak-Vinković, Dijana; Vinković, Mladen; Saldanha, S. Adrian; Ashurst, Jennifer L.; von Delft, Frank; Inoue, Tsuyoshi; Miguel, Ricardo Nunez; Smith, Alison G.; Blundell, Tom L.; Abell, Chris (2001). "Crystal Structure of Escherichia coli Ketopantoate Reductase at 1.7 Å Resolution and Insight into the Enzyme Mechanism". Biochemistry. 40 (48): 14493–14500. doi:10.1021/bi011020w. PMID 11724562.

[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.