Record Information
Version2.0
Creation Date2012-05-31 14:08:05 -0600
Update Date2015-06-03 15:54:51 -0600
Secondary Accession Numbers
  • ECMDB06334
Identification
Name:3-Dehydro-L-gulonate
Description3-Dehydro-L-gulonate is an intermediate in ascorbic acid degradation. It is a substrate for the enzyme 2,3-diketo-L-gulonate reductase. This enzyme catalyzes the reduction of 2,3-diketo-L-gulonate in the presence of NADH, to form 3-keto-L-gulonate. It participates in the reaction: 3-dehydro-L-gulonate + NAD(P)+ = (4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoate + NAD(P)H. Several pathways for the irreversible catabolism of ascorbate have been described. Facultatively aerobic bacteria such as Escherichia coli degrade L-ascorbate by different pathways under aerobic and anaerobic conditions. The anaerobic pathway begins with phosphorylation of ascorbate (mediated by a PTS-type transporter), while the aerobic pathway proceeds via 2,3-dioxo-L-gulonate. Both pathways produce D-xylulose 5-phosphate, a centeral metabolite that is fed into the pentose phosphate pathway.
Structure
Thumb
Synonyms:
  • 3-Dehydro-L-gulonate
  • 3-Dehydro-L-gulonic acid
  • L-Xylo-hex-3-ulosonate
  • L-Xylo-hex-3-ulosonic acid
Chemical Formula:C6H10O7
Weight:Average: 194.1394
Monoisotopic: 194.042652674
InChI Key:WTAHRPBPWHCMHW-LWKDLAHASA-N
InChI:InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,5,7-9,11H,1H2,(H,12,13)/t2-,3+,5-/m0/s1
CAS number:Not Available
IUPAC Name:(2S,4R,5S)-2,4,5,6-tetrahydroxy-3-oxohexanoic acid
Traditional IUPAC Name:3-dehydro-L-gulonic acid
SMILES:OC[C@H](O)[C@@H](O)C(=O)[C@H](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
  • Beta-keto acid
  • Sugar acid
  • Acyloin
  • Alpha-hydroxy acid
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Keto acid
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility105 g/LALOGPS
logP-2.6ALOGPS
logP-2.6ChemAxon
logS-0.27ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.58 m³·mol⁻¹ChemAxon
Polarizability16.3 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0r29-9200000000-bfa5f284c8a99449827aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00ku-4401960000-e7040dc9b253756697acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-4ee99057131bac58d24bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imi-9600000000-abad7f2422697e8886edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-7128eed92da683639fe8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05bu-9800000000-2f48ad5aa2d38b4abf96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap0-9500000000-96092591d92e04b163efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9100000000-833ef232e8c397c98dd3View 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16142
HMDB IDHMDB06334
Pubchem Compound ID439273
Kegg IDC00618
ChemSpider ID388406
Wikipedia IDNot Available
BioCyc ID3-KETO-L-GULONATE
EcoCyc ID3-KETO-L-GULONATE

Enzymes

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.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Catalyzes the phosphorylation of L-xylulose and 3-keto- L-gulonate. Is involved in L-lyxose utilization via xylulose, and may also be involved in the utilization of 2,3-diketo-L-gulonate
Gene Name:
lyx
Uniprot ID:
P37677
Molecular weight:
55155
Reactions
ATP + L-xylulose = ADP + L-xylulose 5-phosphate.
ATP + 3-dehydro-L-gulonate = ADP + 3-dehydro-L-gulonate 6-phosphate.