Ketopantoic acid is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula HOCH
2(CH
3)
2CC(O)CO
2H. At
physiological condition
Physiological condition or, more often "physiological conditions" is a term used in biology, biochemistry, and medicine. It refers to conditions of the external or internal milieu that may occur in nature for that organism or cell system, in contr ...
s, ketopantoic acid exists as its
conjugate base
A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...
, ketopantoate (HOCH
2(CH
3)
2CC(O)CO
2−).
Biosynthetic context
Its biosynthesis proceeds from
ketoisovalerate
α-Ketoisovaleric acid is an organic compound with the formula (CH3)2CHC(O)CO2H. It is a ketoacid. With a melting point just above room temperature, it is usually an oil or semi-solid. The compound is colorless. It is a metabolite of valine an ...
by
hydroxymethylation Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.
Hydroxymethylation with formaldehyde
A common method for hydroxym ...
:
:(CH
3)
2CHC(O)CO
2− + CH
2O → HOCH
2(CH
3)
2CC(O)CO
2−
This conversion is catalyzed by ketopantoate hydroxymethyltransferase, which gives ketopantoate.
Ketopantoate is substrate for
2-dehydropantoate 2-reductase
In enzymology, a 2-dehydropantoate 2-reductase () is an enzyme that catalyzes the chemical reaction
:(R)-pantoate + NADP+ \rightleftharpoons 2-dehydropantoate + NADPH + H+
Thus, the two substrates of this enzyme are (R)-pantoate and NADP+, w ...
, which produces
pantoate
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 a ...
, a precursor to
pantothenic acid, a common prosthetic group.
[{{cite book , doi=10.1016/S0083-6729(01)61005-7, chapter=The Biosynthesis of Coenzyme a in Bacteria, title=Cofactor Biosynthesis, series=Vitamins & Hormones, year=2001, last1=Begley, first1=Tadhg P., last2=Kinsland, first2=Cynthia, last3=Strauss, first3=Erick, volume=61, pages=157–171, pmid=11153265, isbn=9780127098616]
References