Record Information |
---|
Version | 2.0 |
---|
Creation Date | 2012-05-31 13:50:24 -0600 |
---|
Update Date | 2015-06-03 15:53:56 -0600 |
---|
Secondary Accession Numbers | |
---|
Identification |
---|
Name: | GDP-4-Dehydro-6-deoxy-D-mannose |
---|
Description | GDP-4-Dehydro-6-deoxy-D-mannose is an intermediate in fructose and mannose metabolism. GDP-4-Dehydro-6-deoxy-D-mannose is generated by GDP-D-mannose-4,6-dehydratase (GMD). This compound is then converted by the FX protein (GDP-4-keto-6-D-deoxymannose epimerase/GDP-4-keto-6-L-galactose reductase) to GDP-L-fucose. (PMID: 11698403). It is also involved in amino sugar and nucleotide sugar metabolism. (KEGG) |
---|
Structure | |
---|
Synonyms: | - GDP-4-Dehydro-6-deoxy-D-mannose
- GDP-4-Dehydro-6-deoxy-D-talose
- GDP-4-Dehydro-D-rhamnose
- GDP-4-Keto-6-D-deoxymannose
- GDP-4-keto-6-deoxy-α-D-mannose
- GDP-4-keto-6-Deoxy-a-D-mannose
- GDP-4-Keto-6-deoxy-alpha-D-mannose
- GDP-4-Keto-6-deoxy-D-mannose
- GDP-4-keto-6-Deoxy-α-D-mannose
- GDP-4-Keto-6-deoxymannose
- GDP-4-Oxo-6-deoxy-D-mannose
- GDP-4-Oxo-6-deoxymannose
- Guanosine diphosphate-4-keto-6-deoxy-D-mannose
- Guanosine diphosphoric acid-4-keto-6-deoxy-D-mannose
|
---|
Chemical Formula: | C16H23N5O15P2 |
---|
Weight: | Average: 587.3258 Monoisotopic: 587.066588115 |
---|
InChI Key: | PNHLMHWWFOPQLK-BKUUWRAGSA-N |
---|
InChI: | InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1 |
---|
CAS number: | 18186-48-6 |
---|
IUPAC Name: | [({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy})phosphinic acid |
---|
Traditional IUPAC Name: | gdp-4-keto-6-deoxymannose |
---|
SMILES: | C[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@@H](O)C1=O |
---|
Chemical Taxonomy |
---|
Description | belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. |
---|
Kingdom | Organic compounds |
---|
Super Class | Nucleosides, nucleotides, and analogues |
---|
Class | Purine nucleotides |
---|
Sub Class | Purine nucleotide sugars |
---|
Direct Parent | Purine nucleotide sugars |
---|
Alternative Parents | |
---|
Substituents | - Purine nucleotide sugar
- Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-oxopurine
- Hypoxanthine
- Monosaccharide phosphate
- Organic pyrophosphate
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monoalkyl phosphate
- Pyrimidone
- Pyrimidine
- Alkyl phosphate
- Phosphoric acid ester
- Oxane
- Monosaccharide
- Organic phosphoric acid derivative
- N-substituted imidazole
- Tetrahydrofuran
- Vinylogous amide
- Azole
- Imidazole
- Heteroaromatic compound
- Cyclic ketone
- Secondary alcohol
- Ketone
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Hydrocarbon derivative
- Primary amine
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Alcohol
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State: | Solid |
---|
Charge: | -2 |
---|
Melting point: | Not Available |
---|
Experimental Properties: | |
---|
Predicted Properties | |
---|
Biological Properties |
---|
Cellular Locations: | Cytoplasm |
---|
Reactions: | |
---|
SMPDB Pathways: | |
---|
KEGG Pathways: | - Amino sugar and nucleotide sugar metabolism ec00520
- Fructose and mannose metabolism ec00051
- Metabolic pathways eco01100
|
---|
EcoCyc Pathways: | - GDP-L-fucose biosynthesis I (from GDP-D-mannose) PWY-66
|
---|
Concentrations |
---|
| Not Available |
---|
Spectra |
---|
Spectra: | Spectrum Type | Description | Splash Key | |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00mo-7594640000-f6eaffb3b87a7209c04d | View in MoNA |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-002f-6891604000-2d6996a185dcede1dcba | View in MoNA |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS ("GDP-4-Dehydro-6-deoxy-D-mannose,1TMS,#1" TMS) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive | Not Available | View in JSpectraViewer |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0910520000-fcbc13f148251be94ff4 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0910000000-ed550a57c125fee026ee | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-1900000000-a873b451fb06d591cb14 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f79-3901480000-ab8899450fb110bccaf6 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1901000000-c6a3e1a0d5247f947a8a | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pdl-3900000000-148e1fc1e5c7ae57395c | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0000090000-45b44004cbf29fe6aa8f | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-072c-7902450000-9b1901584b05fbc14f34 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fr-2721910000-5a19390a8eaa546bc477 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900030000-a9251fc5a1b28bbacc54 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-2911220000-4e86fd74cab914f8c823 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zgr-9631000000-4a357d49912c73e87853 | View in MoNA |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
---|
1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
---|
|
---|
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
- Roos, C., Kolmer, M., Mattila, P., Renkonen, R. (2002). "Composition of Drosophila melanogaster proteome involved in fucosylated glycan metabolism." J Biol Chem 277:3168-3175. Pubmed: 11698403
- 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
- Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
|
---|
Synthesis Reference: | Oths, Philip J.; Mayer, Robert M.; Floss, Heinz G. Stereochemistry and mechanism of the GDP-mannose dehydratase reaction. Carbohydrate Research (1990), 198(1), 91-100. |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
Links |
---|
External Links: | |
---|