Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:03:42 -0600 |
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Update Date | 2015-10-15 16:13:48 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Deoxyribose 5-phosphate |
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Description | Deoxyribose 5-phosphate is a a metabolite in the pentose phosphate pathway. It can be generated from D-glyceraldehdye-3 phosphate via the enzyme 2-Deoxyribose 5-phosphate aldolase (DERA). Alternately Deoxyribose 5-phosphate can be converted to D-glyceraldehyde-3 phosphate that can then feed into the pentose phosphate pathway. Deoxyribose 5-phosphate can also be generated from 2-Deoxy-D-ribose via the enzyme Ribokinase (EC 2.7.1.15). It has been shown in a number of organisms that deoxynucleosides or deoxyriboses cause the induction of aldolases (such as DERA) involved in their catabolism, leading to the utilisation of the pentose moiety as carbon and energy source. |
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Structure | |
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Synonyms: | - 2-Deoxy-a-D-ribose 5-phosphate
- 2-Deoxy-a-D-ribose 5-phosphoric acid
- 2-Deoxy-a-delta-ribose 5-phosphate
- 2-Deoxy-a-delta-ribose 5-phosphoric acid
- 2-Deoxy-a-δ-ribose 5-phosphate
- 2-Deoxy-a-δ-ribose 5-phosphoric acid
- 2-Deoxy-alpha-D-ribose 5-phosphate
- 2-Deoxy-alpha-D-ribose 5-phosphoric acid
- 2-Deoxy-alpha-delta-ribose 5-phosphate
- 2-Deoxy-alpha-delta-ribose 5-phosphoric acid
- 2-Deoxy-D-ribose 5-phosphate
- 2-Deoxy-D-ribose 5-phosphoric acid
- 2-Deoxy-D-ribose-5-phosphate
- 2-Deoxy-D-ribose-5-phosphoric acid
- 2-Deoxy-α-D-ribose 5-phosphate
- 2-Deoxy-α-D-ribose 5-phosphoric acid
- 2-Deoxy-α-δ-ribose 5-phosphate
- 2-Deoxy-α-δ-ribose 5-phosphoric acid
- 2-Deoxyribose 5-phosphate
- 2-Deoxyribose 5-phosphoric acid
- 2-Deoxyribose-5-p
- 2-Deoxyribose-5-phosphate
- 2-Deoxyribose-5-phosphoric acid
- Deoxy-ribose-5p
- Deoxyribose 5-phosphate
- Deoxyribose 5-phosphoric acid
- Deoxyribose-5-p
- Deoxyribose-5-phosphate
- Deoxyribose-5-phosphoric acid
- DR5P
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Chemical Formula: | C5H11O7P |
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Weight: | Average: 214.1104 Monoisotopic: 214.024239218 |
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InChI Key: | KKZFLSZAWCYPOC-VPENINKCSA-N |
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InChI: | InChI=1S/C5H11O7P/c6-3-1-5(7)12-4(3)2-11-13(8,9)10/h3-7H,1-2H2,(H2,8,9,10)/t3-,4+,5+/m0/s1 |
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CAS number: | 102916-66-5 |
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IUPAC Name: | {[(2R,3S)-3,5-dihydroxyoxolan-2-yl]methoxy}phosphonic acid |
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Traditional IUPAC Name: | [(2R,3S)-3,5-dihydroxyoxolan-2-yl]methoxyphosphonic acid |
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SMILES: | O[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1 |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Pentose phosphates |
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Alternative Parents | |
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Substituents | - Pentose phosphate
- Monosaccharide phosphate
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Tetrahydrofuran
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Solid |
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Charge: | -2 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | |
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EcoCyc Pathways: | - purine deoxyribonucleosides degradation PWY0-1297
- pyrimidine deoxyribonucleosides degradation PWY0-1298
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Concentrations |
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| Concentration | Strain | Media | Growth Status | Growth System | Temperature | Details |
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303± 0 uM | K12 NCM3722 | Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose | Mid-Log Phase | Shake flask and filter culture | 37 oC | PMID: 19561621 |
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Spectra |
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Spectra: | |
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References |
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References: | - Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
- 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
- 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
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Synthesis Reference: | Method of preparing 2-deoxyribose 5-phosphate US Patent |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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