Identification |
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YMDB ID | YMDB00813 |
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Name | L-gulono-1,4-lactone |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | L-Gulonolactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. L-Gulonolactone exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on L-Gulonolactone. |
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Structure | |
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Synonyms | - gamma-gulonolactone
- L-(+)-Gulono-1,4-lactone
- l-gulonic acid gamma-lactone
- L-Gulonic gamma-lactone
- L-Gulono-1,4-lactone
- l-gulono-gamma-lactone
- l-gulonolactone
- g-Gulonolactone
- Γ-gulonolactone
- L-Gulonate g-lactone
- L-Gulonate gamma-lactone
- L-Gulonate γ-lactone
- L-Gulonic acid g-lactone
- L-Gulonic acid γ-lactone
- L-Gulono-g-lactone
- L-Gulono-γ-lactone
- Reduced ascorbate
- Reduced ascorbic acid
- Gulonolactone, (L)-isomer
- Gulonolactone
- Gulonolactone, (D)-isomer
- Dihydroascorbic acid
- L-(+)-Gulonic acid gamma-lactone
- L-(+)-Gulonic acid γ-lactone
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CAS number | 1128-23-0 |
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Weight | Average: 178.14 Monoisotopic: 178.047738052 |
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InChI Key | SXZYCXMUPBBULW-SKNVOMKLSA-N |
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InChI | InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3+,4-,5+/m0/s1 |
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IUPAC Name | (3S,4R,5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one |
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Traditional IUPAC Name | L-gulonolactone |
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Chemical Formula | C6H10O6 |
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SMILES | [H][C@@]1(OC(=O)[C@@H](O)[C@H]1O)[C@@H](O)CO |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Lactones |
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Sub Class | Gamma butyrolactones |
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Direct Parent | Gamma butyrolactones |
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Alternative Parents | |
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Substituents | - Gamma butyrolactone
- Tetrahydrofuran
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- 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 | 0 |
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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 | Not Available |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | Not Available |
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KEGG Pathways | Not Available |
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SMPDB Reactions | Not Available |
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KEGG Reactions | Not Available |
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Concentrations |
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Intracellular Concentrations | Not Available |
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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-MS (4 TMS) | splash10-0gc0-2961000000-10e3ffe56d1491c35d8a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0gc0-2961000000-10e3ffe56d1491c35d8a | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fr2-0930000000-725e277ca1152a7fbc98 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-08fr-9400000000-615dd94b06b3e5e78526 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-0pk9-5359600000-e93f868058ca84374468 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-ec8c949182af76945e86 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9000000000-7a0472476f07853a992b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a70-9300000000-74777b41198e9cd46262 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-06ds-9000000000-2d40464867d71e6c1135 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-01b9-9400000000-d5de17e2c0c42a02efc0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9000000000-0435329cc0eb001898fa | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01t9-1900000000-f47818211aa007edc5f4 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-5900000000-c7c9eb2eaa1f91ac9951 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9100000000-072c615a4ace0aca930a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00or-3900000000-5f8e27814cf4a835d41a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ar0-6900000000-9a9aef2bcc37f743beab | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-9100000000-4892df7d8d2a53c17d7f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-9300000000-cd9f8103b846d70baac0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4l-9000000000-650b3c2ec9303d9b2a96 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-232c502ee9a5b93d5a17 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03fu-1900000000-a9b5237063a8327d87cd | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0296-9500000000-aadb547d81673dce1915 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-08mm-9100000000-0a3f8e5a08a10aa888eb | 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 | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - 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
- Sauer, M., Branduardi, P., Valli, M., Porro, D. (2004). "Production of L-ascorbic acid by metabolically engineered Saccharomyces cerevisiae and Zygosaccharomyces bailii." Appl Environ Microbiol 70:6086-6091.15466554
- Nishikimi, M., Noguchi, E., Yagi, K. (1978). "Occurrence in yeast of L-galactonolactone oxidase which is similar to a key enzyme for ascorbic acid biosynthesis in animals, L-gulonolactone oxidase." Arch Biochem Biophys 191:479-486.369458
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Synthesis Reference: | Not Available |
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External Links: | |
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