Ketopantoic acid

(Redirected from Ketopantoate)

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).

Ketopantoic acid
Names
Other names
4-Hydroxy-3,3-dimethyl-2-oxobutanoic acid; 2-Dehydropantoic acid
Identifiers
3D model (JSmol)
2242422
ChEBI
ChemSpider
DrugBank
KEGG
  • InChI=1S/C6H10O4/c1-6(2,3-7)4(8)5(9)10/h7H,3H2,1-2H3,(H,9,10)
    Key: PKVVTUWHANFMQC-UHFFFAOYSA-N
  • CC(C)(CO)C(=O)C(=O)O
Properties
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).

Biosynthetic context

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

References

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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.