2-KETO-L-GULONIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H10O7
Molecular Weight	194.1394
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O

InChI

InChIKey=VBUYCZFBVCCYFD-NUNKFHFFSA-N

InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-4,7-10H,1H2,(H,12,13)/t2-,3+,4-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23356419 | https://www.trc-canada.com/product-detail/?K191320 | https://www.ncbi.nlm.nih.gov/pubmed/22734896

2-keto-L-gulonic acid (2-KLG) is a direct precursor (lactone) of L-ascorbic acid (vitamin C). 2-Keto-L-gulonic Acid is used in biological studies for the formation of sorbitol metabolism by Acetobacter melanogenus. Ketogulonigenium vulgare has long been used in industry to produce 2-keto-L-gulonic acid (2KGA).

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Bacterial polysaccharides as vaccines--immunity and chemical characterization.	2001	14533815
Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution.	2001	11721885
N-unsubstituted glucosamine in heparan sulfate of recycling glypican-1 from suramin-treated and nitrite-deprived endothelial cells. mapping of nitric oxide/nitrite-susceptible glucosamine residues to clustered sites near the core protein.	2001 Feb 9	11110783
[Preclinical toxicological study of D-glucuronic acid].	2001 Jan-Feb	11544811
Influence of ethanol on metabolism of methamphetamine in rats including hair analysis.	2001 Jun	11494586
Enhanced multispecificity of arabidopsis vacuolar multidrug resistance-associated protein-type ATP-binding cassette transporter, AtMRP2.	2001 Mar 23	11115509
Toward a biotechnological heparin through combined chemical and enzymatic modification of the Escherichia coli K5 polysaccharide.	2001 Oct	11668413
Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport.	2001 Oct 1	11585759
(1)H nuclear magnetic resonance spectroscopic analysis for determination of glucuronic and iduronic acids in dermatan sulfate, heparin, and heparan sulfate.	2001 Oct 1	11567526
Toxicological relevance of the multidrug resistance protein 1, MRP1 (ABCC1) and related transporters.	2001 Oct 5	11557126
Drug resistance caused by multidrug resistance-associated proteins.	2002	11990783
Increase in gap-junctional intercellular communications (GJIC) of normal human dermal fibroblasts (NHDF) on surfaces coated with high-molecular-weight hyaluronic acid (HMW HA).	2002 Jun 15	11948512
Periodate-treated, non-anticoagulant heparin-carrying polystyrene (NAC-HCPS) affects angiogenesis and inhibits subcutaneous induced tumour growth and metastasis to the lung.	2002 Jun 5	12087470
Acylated triterpenoid saponins from the stem bark of Foetidia africana.	2002 Nov	12444677
Optimization of exopolysaccharide production by Tremella mesenterica NRRL Y-6158 through implementation of fed-batch fermentation.	2002 Oct	12355316
Determination of hexafluoroisopropanol, a sevoflurane urinary metabolite, by 9-fluorenylmethyl chloroformate derivatization.	2002 Sep 5	12138006
[Lectin activity of antitumor substances synthesized by Bacillus subtilis B-7025].	2002 Sep-Oct	12557488
Analysis of reducing carbohydrates by reductive tryptamine derivatization prior to micellar electrokinetic capillary chromatography.	2003 Dec 3	14640563
Structural requirements for functional interaction of glutathione tripeptide analogs with the human multidrug resistance protein 1 (MRP1).	2003 Feb	12538817
Differential modulation of the human liver conjugate transporters MRP2 and MRP3 by bile acids and organic anions.	2003 Jun 27	12704183
Cryptococcus nemorosus sp. nov. and Cryptococcus perniciosus sp. nov., related to Papiliotrema Sampaio et al. (Tremellales).	2003 May	12807220
Specificity of yeast (Saccharomyces cerevisiae) in removing carbohydrates by fermentation.	2003 May 1	12706980
Structural analysis of the carbohydrate backbone of Vibrio parahaemolyticus O2 lipopolysaccharides.	2003 May 1	12706972
The structure of the glycopeptides from the fish pathogen Flavobacterium columnare.	2003 Nov 14	14670723
PathMAPA: a tool for displaying gene expression and performing statistical tests on metabolic pathways at multiple levels for Arabidopsis.	2003 Nov 7	14604444
Identification and functional characterization of the natural variant MRP3-Arg1297His of human multidrug resistance protein 3 (MRP3/ABCC3).	2004 Apr	15083066
Design and synthesis of dimeric heparinoid mimetics.	2004 Dec 24	15609950
Design, synthesis, and evaluation of a liposaccharide drug delivery agent: application to the gastrointestinal absorption of gentamicin.	2004 Feb 26	14971905
Pharmacokinetics in mice and growth-inhibitory properties of the putative cancer chemopreventive agent resveratrol and the synthetic analogue trans 3,4,5,4'-tetramethoxystilbene.	2004 Feb 9	14760392
Crystal structure of unsaturated glucuronyl hydrolase, responsible for the degradation of glycosaminoglycan, from Bacillus sp. GL1 at 1.8 A resolution.	2004 Jul 23	15148314
Crystallization and preliminary X-ray analysis of heparinase II from Pedobacter heparinus.	2004 Sep	15333943
Modulation of the heparanase-inhibiting activity of heparin through selective desulfation, graded N-acetylation, and glycol splitting.	2005 Apr 1	15647251
Candida digboiensis sp. nov., a novel anamorphic yeast species from an acidic tar sludge-contaminated oilfield.	2005 Mar	15774693
Up-regulation of human myo-inositol oxygenase by hyperosmotic stress in renal proximal tubular epithelial cells.	2005 May 20	15778219
Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition.	2005 May 9	15882454

Patents

Sample Use Guides

In Vivo Use Guide

Rats which excreted daily 0.9 = 0.02 mg of L-ascorbic acid. received by intraperitoneal injection 90 mg of 2-keto-L-gulonic acid and a week later 90 mg of methyl 2-keto-L-gulonate.

Route of Administration: Intraperitoneal

In Vitro Use Guide

Unknown

Name

Type

Language

2-KETO-L-GULONIC ACID

Common Name

English

2-OXO-L-GULONIC ACID

Common Name

English

L-SORBOSONIC ACID

Common Name

English

2-KETO-L-GULONIC ACID [MI]

Common Name

English

L-XYLO-HEX-2-ULOSONIC ACID

Systematic Name

English

ASCORBIC ACID IMPURITY C [EP IMPURITY]

Common Name

English

L-XYLO-2-HEXULOSONIC ACID

Common Name

English

Code System Code Type Description

CHEBI

19543