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2,3-Diketo-L-gulonate (M2MDB000677)

Record Information
Version2.0
Creation Date2012-05-31 14:08:43 -0600
Update Date2015-09-17 15:41:19 -0600
Secondary Accession Numbers
  • ECMDB06511
Identification
Name:2,3-Diketo-L-gulonate
Description2,3-Diketo-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 2,3-Diketo-L-gulonate is produced from Dehydroascorbate and then converted to L-Xylonate via the enzyme Lyases (EC 4.1.1.-).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoate
  • (4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoic acid
  • 2,3-Diketo-L gulonate
  • 2,3-Diketo-L gulonic acid
  • 2,3-Diketo-L-gulonate
  • 2,3-Diketo-L-gulonic acid
  • 2,3-Diketogulonate
  • 2,3-Diketogulonic acid
  • Diketogulonate
  • Diketogulonic acid
  • DKG
  • L-Threo-2,3-hexodiulosonate
  • L-Threo-2,3-hexodiulosonic acid
  • L-Threo-hexo-2,3-diulosonate
  • L-Threo-hexo-2,3-diulosonic acid
  • L-Xylo-hex-2-enonate
  • L-Xylo-hex-2-enonic acid
Chemical Formula:C6H8O7
Weight:Average: 192.1235
Monoisotopic: 192.02700261
InChI Key:GJQWCDSAOUMKSE-SCQFTWEKSA-N
InChI:InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/t2-,3?/m0/s1
CAS number:Not Available
IUPAC Name:(4S,5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid
Traditional IUPAC Name:(4S,5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid
SMILES:OC[C@H](O)C(O)C(=O)C(=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Medium-chain keto acid
  • Sugar acid
  • Beta-keto acid
  • Monosaccharide
  • Keto acid
  • Beta-hydroxy ketone
  • Alpha-diketone
  • Alpha-keto acid
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility59.9 g/LALOGPS
logP-1.8ALOGPS
logP-1.6ChemAxon
logS-0.51ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.04 m³·mol⁻¹ChemAxon
Polarizability15.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2,3-Diketo-L-gulonate + Hydrogen ion + NADH > 3-Dehydro-L-gulonate + NAD
3-Dehydro-L-gulonate + NAD <> 2,3-Diketo-L-gulonate + NADH + Hydrogen ion
3-Dehydro-L-gulonate + NADP <> 2,3-Diketo-L-gulonate + NADPH + Hydrogen ion
dehydroascorbate (bicyclic form) > 2,3-Diketo-L-gulonate + Hydrogen ion
2,3-Diketo-L-gulonate > 2-carboxy-L-xylonolactone
3-Dehydro-L-gulonate + NAD < Hydrogen ion + 2,3-Diketo-L-gulonate + NADH
3-Dehydro-L-gulonate + NAD + NADP <> 2,3-Diketo-L-gulonate + NADH + NADPH + Hydrogen ion
2,3-Diketo-L-gulonate + NADH + Hydrogen ion + 2,3-Diketo-L-gulonate > 3-Dehydro-L-gulonate + NAD
2,3-Diketo-L-gulonate + Hydrogen ion + 2,3-Diketo-L-gulonate > Carbon dioxide + Xylulose 5-phosphate + Xylulose 5-phosphate
SMPDB Pathways:
Ascorbate metabolismPW000793 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Ascorbate and aldarate metabolism ec00053
  • Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:
  • L-ascorbate degradation II (bacterial, aerobic) PWY-6961
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-1900000000-9515a38ec1b55e533d9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-9800000000-a604d8f9066490c7fa9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-338bda8823075f3222b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fnl-6900000000-db80f07e41960f9da2bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pwi-9600000000-7fa5a5d582918ac80f13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9100000000-6267bad594d456dca576View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15622
HMDB IDHMDB06511
Pubchem Compound ID440390
Kegg IDC04575
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD-334
EcoCyc IDCPD-334

Enzymes

Protein Details
1. 2,3-diketo-L-gulonate reductase
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the reduction of 2,3-diketo-L-gulonate in the presence of NADH, to form 3-keto-L-gulonate
Gene Name:
dlgD
Uniprot ID:
P37672
Molecular weight:
36572
Reactions
3-dehydro-L-gulonate + NAD(P)(+) = (4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoate + NAD(P)H.
Protein Details
2. 3-keto-L-gulonate-6-phosphate decarboxylase sgbH
General function:
Involved in catalytic activity
Specific function:
Catalyzes the decarboxylation of 3-keto-L-gulonate-6-P into L-xylulose-5-P. May be involved in the utilization of 2,3- diketo-L-gulonate
Gene Name:
sgbH
Uniprot ID:
P37678
Molecular weight:
23445
Reactions
3-dehydro-L-gulonate 6-phosphate = L-xylulose 5-phosphate + CO(2).

Transporters

Protein Details
1. 2,3-diketo-L-gulonate TRAP transporter small permease protein yiaM
General function:
Carbohydrate transport and metabolism
Specific function:
Part of the tripartite ATP-independent periplasmic (TRAP) transport system yiaMNO involved in the uptake of 2,3- diketo-L-gulonate
Gene Name:
yiaM
Uniprot ID:
P37674
Molecular weight:
17516
Protein Details
2. 2,3-diketo-L-gulonate TRAP transporter large permease protein yiaN
General function:
Carbohydrate transport and metabolism
Specific function:
Part of the tripartite ATP-independent periplasmic (TRAP) transport system yiaMNO involved in the uptake of 2,3- diketo-L-gulonate
Gene Name:
yiaN
Uniprot ID:
P37675
Molecular weight:
45368