Pantoic acid
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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 | |
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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 |
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),[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
External links
- Media related to Pantoic acid at Wikimedia Commons
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