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Thioproline

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

  1. ^ 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.
  2. ^ "L-Thioproline". pubchem.ncbi.nlm.nih.gov.
  3. ^ Ratner, Sarah; Clarke, H. T. (1937). "The Action of Formaldehyde upon Cysteine". Journal of the American Chemical Society. 59: 200–206. doi:10.1021/ja01280a050.
  4. ^ 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.
  5. ^ 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.