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Identification |
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YMDB ID | YMDB00378 |
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Name | L-Proline |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Proline (abbreviated as Pro or P) is an alpha-amino acid or more technically an iminio acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is classified as a polar amino acid, because of the hydrophilic nature of its cycloalkyl side chain. It is unique among the 20 protein-forming amino acids in that the alpha-amino group is secondary. The distinctive cyclic structure of proline's side chain locks its φ backbone dihedral angle at approximately −75°, giving proline an exceptional conformational rigidity compared to other amino acids. Proline is biosynthetically derived from the amino acid L-glutamate and its immediate precursor is the imino acid (S)-1-pyrroline-5-carboxylate (P5C). Enzymes involved in a typical biosynthesis include: Glutamate kinase; Glutamate dehydrogenase and Pyrroline-5-carboxylate reductase. Proline and its derivatives are often used as asymmetric catalysts in organic reactions. The CBS reduction and proline catalysed aldol condensation are prominent examples. In brewing, proteins rich in proline combine with polyphenols to produce haze (turbidity). Proline is typically the most abundant amino acid found in wine. During fermentation of wine most of the amino acids are practically depleted from the grape juice/ grape must (the juice component including skins, seeds and stems) by the time the first 30 g of sugar have been fermented. Yeast make use of alanine and argnine acids and ammonium (slightly) after the depletion of the other amino acids. Yeast then assimilate arginine only after the disappearance of ammonium from the grape must/juice. Yeasts do not utilize proline during fermentation although it is one of the principle amino acids found in must. During fermentation, yeasts assimilate between 1 and 2 g/L of amino acids. Towards the end of fermentation, yeasts excrete significant but variable amounts of different amino acids. Finally at the end of alcoholic fermentation, a few hundred mg/L of amino acids remain with proline generally represents half. |
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Structure | |
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Synonyms | - (-)-(S)-Proline
- (-)-2-Pyrrolidinecarboxylate
- (-)-2-Pyrrolidinecarboxylic acid
- (-)-Proline
- (S)-(-)-Proline
- (S)-(-)-Pyrrolidine-2-carboxylate
- (S)-(-)-Pyrrolidine-2-carboxylic acid
- (S)-2-Carboxypyrrolidine
- (S)-2-Pyrralidinecarboxylate
- (S)-2-Pyrralidinecarboxylic acid
- (S)-2-Pyrrolidinecarboxylate
- (S)-2-Pyrrolidinecarboxylic acid
- (S)-Proline
- 2-Pyrrolidinecarboxylate
- 2-Pyrrolidinecarboxylic acid
- Proline
- (2S)-Pyrrolidine-2-carboxylic acid
- (S)-Pyrrolidine-2-carboxylic acid
- L-(-)-Proline
- L-alpha-Pyrrolidinecarboxylic acid
- L-Prolin
- L-Pyrrolidine-2-carboxylic acid
- P
- Prolina
- Prolinum
- (2S)-Pyrrolidine-2-carboxylate
- (S)-Pyrrolidine-2-carboxylate
- L-a-Pyrrolidinecarboxylate
- L-a-Pyrrolidinecarboxylic acid
- L-alpha-Pyrrolidinecarboxylate
- L-Α-pyrrolidinecarboxylate
- L-Α-pyrrolidinecarboxylic acid
- L-Pyrrolidine-2-carboxylate
- L Proline
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CAS number | 147-85-3 |
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Weight | Average: 115.1305 Monoisotopic: 115.063328537 |
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InChI Key | ONIBWKKTOPOVIA-BYPYZUCNSA-N |
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InChI | InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1 |
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IUPAC Name | (2S)-pyrrolidine-2-carboxylic acid |
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Traditional IUPAC Name | L-proline |
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Chemical Formula | C5H9NO2 |
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SMILES | [H]OC(=O)[C@@]1([H])N([H])C([H])([H])C([H])([H])C1([H])[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Proline and derivatives |
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Alternative Parents | |
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Substituents | - Proline or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Pyrrolidine carboxylic acid
- Pyrrolidine carboxylic acid or derivatives
- Pyrrolidine
- Amino acid
- Carboxylic acid
- Secondary aliphatic amine
- Monocarboxylic acid or derivatives
- Secondary amine
- Organoheterocyclic compound
- Azacycle
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Organopnictogen compound
- Organic oxide
- Carbonyl group
- Organic nitrogen compound
- Hydrocarbon derivative
- 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 | 0 |
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Melting point | 221 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 162 mg/mL at 25 oC [MERCK INDEX (1996)] | PhysProp | LogP | -2.54 [HANSCH,C ET AL. (1995)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - extracellular
- mitochondrion
- cytoplasm
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Organoleptic Properties | |
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SMPDB Pathways | |
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KEGG Pathways | Arginine and proline metabolism | ec00330 |  |
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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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1075 ± 54 µM | YEB media with 0.5 mM glucose | aerobic | Baker's yeast | Experimentally Determined Not Available | 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 (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0006-0910000000-a9127c0e370afb80259b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-000f-0910000000-3195f21e625520d51316 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0006-0900000000-119af746c347969e8ae7 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-006x-8900000000-b31beabb1ed6235e7145 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-00di-9100000000-c1c67bc521741ee891cb | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0006-1900000000-84e6fb318323fd0261b1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00fu-9000000000-716c3d01b301162863b6 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-0900000000-0d7354201ed866c87b13 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0006-0910000000-a9127c0e370afb80259b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000f-0910000000-3195f21e625520d51316 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0006-0900000000-119af746c347969e8ae7 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-QQ (Non-derivatized) | splash10-001i-1920000000-09006ee4e7a137d8a45a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-006x-8900000000-b31beabb1ed6235e7145 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0006-1900000000-84e6fb318323fd0261b1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00xs-8910000000-74b0c34ca5fd7c85f1d9 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00di-9100000000-c1c67bc521741ee891cb | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00fu-9000000000-d203e3dfb0701403a75b | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9000000000-56471980a375d26046ca | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-03di-0900000000-2c23774af5f6a0c217d5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03di-0900000000-d89c1e626ef24a79c89f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-03di-1900000000-fc27094f2eb75e65b438 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-03di-0900000000-e1d0a4b20419dc7bae92 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-0900000000-2c23774af5f6a0c217d5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-0900000000-d89c1e626ef24a79c89f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-1900000000-fc27094f2eb75e65b438 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-03di-0900000000-e1d0a4b20419dc7bae92 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00xr-9600000000-ba51a901e786b1a4663e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-f72e2f3812225708fc56 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9000000000-59887da6580f63bcc1c5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-00fu-9000000000-c69dcaf7cb2d1e9d285e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0930000000-984f9a23ebfe28f95017 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-9000000000-f75575cac28a54aa923d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-9000000000-221cfb8c82f3df76eb51 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-e5741fd9870218d57caf | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-6bc9b4e775be37fa18d9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-9000000000-a8eb419b26655a6a1dab | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00di-9000000000-873ee03b61d1ffcae70f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0900000000-61d583960651669fb9e6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-014i-1900000000-3221c23504b8847abf8d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-9100000000-8169367f5127c57fae12 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00di-9000000000-f704eb8402fcacfccd18 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-00di-9000000000-ccd74eea36efab2cbab8 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-00di-9000000000-9f214692cd39a6581813 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H 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
- Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
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Synthesis Reference: | Itoh, Tamio. Synthesis of L-proline from L-glutamine. Bulletin of the Chemical Society of Japan (1963), 36(1), 25-9 |
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External Links: | |
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