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16682

Sigma-Aldrich

(R)-Pantoic acid sodium salt

≥95% (GC)

Synonym(s):

(2R)-2,4-Dihydroxy-3,3-dimethylbutanoic acid monosodium salt, (R)-2,4-Dihydroxy-3,3-dimethylbutyric acid sodium salt, Sodium (R)-pantoate, Sodium D-pantoate

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About This Item

Empirical Formula (Hill Notation):
C6H11NaO4
CAS Number:
60979-68-2
Molecular Weight:
170.14
Beilstein:
6119584
MDL number:
MFCD29079001
UNSPSC Code:
12352106
NACRES:
NA.25
Pricing and availability is not currently available.

Quality Level

100

Assay

≥95% (GC)

optical activity

[α]/D 8.0±1.0°, c = 1 in H2O

storage temp.

−20°C

SMILES string

[Na+].[O-]C(=O)[C@H](O)C(CO)(C)C

InChI

1S/C6H12O4.Na/c1-6(2,3-7)4(8)5(9)10;/h4,7-8H,3H2,1-2H3,(H,9,10);/q;+1/p-1/t4-;/m0./s1

InChI key

XTIMSSMEPPKSQD-WCCKRBBISA-M

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Biochem/physiol Actions

(R)-Pantoic acid is an intermediate in the phosphopantothenate biosynthesis pathway for the de novo synthesis of R-pantothenate (vitamin B5) from valine in plants and microorganisms.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0067
BCCK6796
BCCH6529
BCCG7283
BCCF7517

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Hiroya Tomita et al.
Journal of bacteriology, 194(19), 5434-5443 (2012-08-07)
Although bacteria and eukaryotes share a pathway for coenzyme A (CoA) biosynthesis, we previously clarified that most archaea utilize a distinct pathway for the conversion of pantoate to 4'-phosphopantothenate. Whereas bacteria/eukaryotes use pantothenate synthetase and pantothenate kinase (PanK), the hyperthermophilic
13C-NMR and 1H-1H NOEs of Coenzyme A: conformation of the pantoic acid moiety.
Dordine, R.L., et al.
Bioorganic Chemistry, 23, 169-181 (1995)
Michael Rothmann et al.
Journal of the American Chemical Society, 135(16), 5962-5965 (2013-04-05)
Pantetheine and its corresponding disulfide pantethine play a key role in metabolism as building blocks of coenzyme A (CoA), an essential cofactor utilized in ~4% of primary metabolism and central to fatty acid, polyketide, and nonribosomal peptide synthases. Using a
Analysis of stereochemistry of enzymically formed pantoyl lactone or pantoic acid by gas chromatography and circular dichroism.
D R Wilken et al.
Analytical biochemistry, 112(1), 9-16 (1981-03-15)
Dayong Si et al.
Applied microbiology and biotechnology, 93(4), 1619-1625 (2011-11-16)
Ketopantoic acid (KPA) reductase catalyzes the stereospecific reduction of ketopantoic acid to D-pantoic acid. Based on the N-terminal amino acid sequence of KPA reductase from Stenotrophomonas maltophilia 845, the KPA reductase gene was cloned from S. maltophilia NBRC14161 and sequenced.

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