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Identification |
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YMDB ID | YMDB00073 |
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Name | Glycerol 3-phosphate |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phosphate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate(GA3P) by triose phosphate isomerase(TIM), and feed into glycolysis. [Wikipedia] |
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Structure | |
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Synonyms | - (R)-glycerol 1-phosphate
- 1-(dihydrogen phosphate) Glycerol
- 1-Glycerophosphate
- 1-Glycerophosphorate
- 1-Glycerophosphoric acid
- 1-phosphoglycerol
- 1,2,3-propanetriol, 1-(dihydrogen phosphate)
- 2,3-dihydroxypropyl dihydrogen phosphate
- 2,3-hydroxy-1-propyl dihydrogen phosphate
- 3-Glycerophosphate
- a-Glycerophosphate
- a-Glycerophosphorate
- a-Glycerophosphoric acid
- a-Phosphoglycerol
- alpha-Glycerophosphate
- alpha-Glycerophosphorate
- alpha-Glycerophosphoric acid
- alpha-Phosphoglycerol
- D-(glycerol 1-phosphate)
- D-Glycerol 1-phosphate
- dihydrogen a-glycerophosphate
- DL-a-Glycerol phosphate
- DL-a-Glycerophosphate
- DL-a-Glycerophosphorate
- DL-a-Glycerophosphoric acid
- DL-a-Glyceryl phosphate
- DL-alpha-Glycerol phosphate
- DL-alpha-Glycerophosphate
- DL-alpha-Glycerophosphorate
- DL-alpha-Glycerophosphoric acid
- DL-alpha-Glyceryl phosphate
- DL-Glycerol 1-phosphate
- DL-Glycerol 3-phosphate
- Glycerol 1-phosphate
- Glycerol a-phosphate
- glycerol alpha-phosphate
- Glycerol monophosphate
- Glycerol-3-phosphate
- Glycerophosphate
- Glycerophosphorate
- Glycerophosphoric acid
- Glycerophosphoric acid I
- Glyceryl phosphate
- Glyceryl phosphic acid
- L-(glycerol 3-phosphate)
- PG
- phosphatidyl glycerol
- phosphoric acid mono-((R)-2,3-dihydroxy-propyl) ester
- Phosphorsaeure-mono-((R)-2,3-dihydroxy-propylester)
- sn-glycerol 3-phosphate
- SN-GLYCEROL-3-PHOSPHATE
- sn-Gro-1-P
- (R)-Glycerol 1-phosphoric acid
- D-(Glycerol 1-phosphoric acid)
- D-Glycerol 1-phosphoric acid
- Glycerol-3-phosphoric acid
- L-(Glycerol 3-phosphoric acid)
- Phosphate mono-((R)-2,3-dihydroxy-propyl) ester
- sn-GLYCEROL-3-phosphoric acid
- Glycerol 3-phosphoric acid
- alpha-Glycerophosphoric acid, (DL)-isomer
- alpha-Glycerophosphoric acid, (R)-isomer
- alpha-Glycerophosphoric acid, (S)-isomer
- alpha-Glycerophosphoric acid, 1,2,3-propanetriol-1-(18)O,3-(dihydrogen phosphate)-labeled
- alpha-Glycerophosphoric acid, 1,2,3-propanetriol-2-(18)O,3-(dihydrogen phosphate)-labeled
- alpha-Glycerophosphoric acid, fe salt
- alpha-Glycerophosphoric acid, fe(+3) salt (3:2)
- alpha-Glycerophosphoric acid, calcium salt
- alpha-Glycerophosphoric acid, disodium salt
- alpha-Glycerophosphoric acid, disodium salt (+-)-isomer
- alpha-Glycerophosphoric acid, disodium salt hexahydrate(+-)-isomer
- alpha-Glycerophosphoric acid, monocalcium salt
- alpha-Glycerophosphoric acid, monocalcium salt (S)-isomer
- alpha-Glycerophosphoric acid, monomagnesium salt
- alpha-Glycerophosphoric acid, sodium salt
- Disodium glycerophosphate
- Sodium glycerophosphate
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CAS number | 17989-41-2 |
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Weight | Average: 172.0737 Monoisotopic: 172.013674532 |
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InChI Key | AWUCVROLDVIAJX-GSVOUGTGSA-N |
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InChI | InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1 |
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IUPAC Name | [(2R)-2,3-dihydroxypropoxy]phosphonic acid |
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Traditional IUPAC Name | 3-phosphoglycerol |
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Chemical Formula | C3H9O6P |
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SMILES | [H]OC([H])([H])[C@@]([H])(O[H])C([H])([H])OP(=O)(O[H])O[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | Glycerophosphates |
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Direct Parent | Glycerophosphates |
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Alternative Parents | |
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Substituents | - Sn-glycerol-3-phosphate
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Secondary alcohol
- 1,2-diol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | 102-104 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 1000 mg/mL [MERCK INDEX (1996); readily soluble] | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - mitochondrion
- lipid particle
- endoplasmic reticulum
- cytoplasm
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Organoleptic Properties | Not Available |
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SMPDB Pathways | Cardiolipin Biosynthesis | PW002431 | | Cardiolipin Biosynthesis CL(10:0/10:0/10:0/28:0) | PW003484 | | Cardiolipin Biosynthesis CL(10:0/10:0/10:0/30:0) | PW003501 | | Cardiolipin Biosynthesis CL(10:0/10:0/12:0/26:0) | PW003502 | | Cardiolipin Biosynthesis CL(10:0/10:0/12:0/28:0) | PW003503 | |
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KEGG Pathways | |
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SMPDB Reactions |
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KEGG Reactions |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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0.0 ± 0.0 µM | Minimal medium supplemented with ammonia salts and glucose | aerobic;resting cells | Baker's yeast | PMID: 4578278 | Conversion Details Here |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0uea-0932000000-726f422c76a193edf232 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0uea-0932000000-726f422c76a193edf232 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-0zgj-1976000000-019de1fa6314b95ef7fe | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01ot-9300000000-a435ec7fb966f8ddc1a2 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0230-9080000000-9f48133c7a08fb549acd | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0002-9200000000-bf06c1d1e56cb8853243 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00kr-9200000000-ffce45222cab00a0c302 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001j-9000000000-7689cca8f9c9a12d9e75 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0902000000-00e3a7e1ee10fbd8b03e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-1a40c90fd2eb656ddf5c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0002-9000000000-f9bc5f552db38767c437 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0002-0920000000-72f8b96355726dd3a5b1 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-0901000000-2c3a8ed438d7ca0fa049 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-a3549fb5ec2675fbf615 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0002-9000000000-096e2ba9a6ef6fd20d88 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0002-0930000000-171708905bad289d6031 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-0925110000-c1ced10d34f533b3fa1f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03di-0900000000-4ee8a36492a451beda75 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-9000000000-de2aacfb81476c7755e5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-0900000000-dd342482ade09e9ce749 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0fkc-0917520000-d61e6034525ac5f7588d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004i-9000000000-d537d3f23f3d9a789c20 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-0900000000-2f1ca45b50402f6e62df | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0009000000-5606781224d6ab5caed3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0pi0-1900000000-75b6ed57a4c9cd6378b4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0a59-6900000000-1c46fbda1468f6fd803c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-0a5c-9400000000-305e9a2554d8c3274f32 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-007o-9000000000-d11ad04a048c3dca25de | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-00mo-9000000000-7b779b4be184b5b26b6a | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-5900000000-297dbde751110233eca5 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Norbeck, J., Pahlman, A. K., Akhtar, N., Blomberg, A., Adler, L. (1996). "Purification and characterization of two isoenzymes of DL-glycerol-3-phosphatase from Saccharomyces cerevisiae. Identification of the corresponding GPP1 and GPP2 genes and evidence for osmotic regulation of Gpp2p expression by the osmosensing mitogen-activated protein kinase signal transduction pathway." J Biol Chem 271:13875-13881.8662716
- Andre, L., Hemming, A., Adler, L. (1991). "Osmoregulation in Saccharomyces cerevisiae. Studies on the osmotic induction of glycerol production and glycerol-3-phosphate dehydrogenase (NAD+)" FEBS Lett 286:13-17.1864360
- Fernandez-Murray, J. P., McMaster, C. R. (2005). "Glycerophosphocholine catabolism as a new route for choline formation for phosphatidylcholine synthesis by the Kennedy pathway." J Biol Chem 280:38290-38296.16172116
- Athenstaedt, K., Weys, S., Paltauf, F., Daum, G. (1999). "Redundant systems of phosphatidic acid biosynthesis via acylation of glycerol-3-phosphate or dihydroxyacetone phosphate in the yeast Saccharomyces cerevisiae." J Bacteriol 181:1458-1463.10049376
- Fisher, E., Almaguer, C., Holic, R., Griac, P., Patton-Vogt, J. (2005). "Glycerophosphocholine-dependent growth requires Gde1p (YPL110c) and Git1p in Saccharomyces cerevisiae." J Biol Chem 280:36110-36117.16141200
- Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
- Zheng, Z., Zou, J. (2001). "The initial step of the glycerolipid pathway: identification of glycerol 3-phosphate/dihydroxyacetone phosphate dual substrate acyltransferases in Saccharomyces cerevisiae." J Biol Chem 276:41710-41716.11544256
- Albertyn, J., Hohmann, S., Thevelein, J. M., Prior, B. A. (1994). "GPD1, which encodes glycerol-3-phosphate dehydrogenase, is essential for growth under osmotic stress in Saccharomyces cerevisiae, and its expression is regulated by the high-osmolarity glycerol response pathway." Mol Cell Biol 14:4135-4144.8196651
- Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
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Synthesis Reference: | Rios-Mercadillo, Victor M.; Whitesides, George M. Enzymic synthesis of sn-glycerol 3-phosphate. Journal of the American Chemical Society (1979), 101(19), 5828-9. |
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