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Thioproline
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| Names | |
|---|---|
| Other names
(R)-1,3-Thiazolidin-3-ium-4-carboxylate
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | H-Thz-OH |
| ChEBI |
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| ChEMBL | |
| ChemSpider |
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| DrugBank | |
| ECHA InfoCard | 100.006.498 |
| EC Number |
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PubChem CID
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| UNII |
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CompTox Dashboard (EPA)
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| Properties | |
| C4H7NO2S | |
| Molar mass | 133.17 g·mol−1 |
| Appearance | white solid |
| Density | 1.578 g/cm3[1] |
| Melting point | 196.5 °C (385.7 °F; 469.6 K) |
| Hazards | |
| GHS labelling:[2] | |
 
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| Danger | |
| H301, H312, H315, H319, H332, H335 | |
| P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thioproline is a nonproteinogenic amino acid with the formula (CH2SCH2NHCH)CO2H, although it crystallizes as the zwitterion (CH2SCH2NH+2CH)CO−2. It consists of a 1,3-thiazolidine ring ( (CH2SCH2NHCH2)) substituted with a carboxylic acid. It is synthesized by reaction of formaldehyde and cysteine.[3] It occurs in nature, but rarely.[4] It forms a coordination complex with cobalt.[5]
References
[edit]- ^ Grant, Neil; Ward, Mark F.; Jaspars, Marcel; Harrison, William T. A. (2001). "( R )-1,3-Thiazolidin-3-ium-4-carboxylate". Acta Crystallographica Section E: Structure Reports Online. 57 (8): o697–o699. Bibcode:2001AcCrE..57O.697G. doi:10.1107/S1600536801010947.
- ^ "L-Thioproline". pubchem.ncbi.nlm.nih.gov.
- ^ Ratner, Sarah; Clarke, H. T. (1937). "The Action of Formaldehyde upon Cysteine". Journal of the American Chemical Society. 59 (1): 200–206. Bibcode:1937JAChS..59..200R. doi:10.1021/ja01280a050.
- ^ Zierer, Jonas; Jackson, Matthew A.; Kastenmüller, Gabi; Mangino, Massimo; Long, Tao; Telenti, Amalio; Mohney, Robert P.; Small, Kerrin S.; Bell, Jordana T.; Steves, Claire J.; Valdes, Ana M.; Spector, Tim D.; Menni, Cristina (2018). "The fecal metabolome as a functional readout of the gut microbiome". Nature Genetics. 50 (6): 790–795. doi:10.1038/s41588-018-0135-7. PMC 6104805. PMID 29808030.
- ^ Gainsford, GJ; Jackson, WG; Sargeson, AM; Watson, AD (1980). "(4R)-Thiazolidine-4-carboxylic acid: Ligand specificity and the synthesis and X-ray structure of a cobalt(III) complex". Australian Journal of Chemistry. 33 (6): 1213. doi:10.1071/CH9801213.