Thioproline

Thioproline
Names
	Other names (R)-1,3-Thiazolidin-3-ium-4-carboxylate
Identifiers
CAS Number	444-27-9 ; L: 34592-47-7 ;
3D model (JSmol)	L: Interactive image ; zitteranion: Interactive image ;
Abbreviations	H-Thz-OH
ChEBI	L: CHEBI:45171 ;
ChEMBL	L: ChEMBL1235440 ;
ChemSpider	L: 84120 ;
DrugBank	DB02846 ;
ECHA InfoCard	100.047.355
EC Number	L:256-240-3;
PubChem CID	L: 93176 ; zitteranion: 6973609 ;
UNII	L: KL096K0KXL ;
CompTox Dashboard (EPA)	DTXSID3046536 ;
	InChI L:InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1 Key: DZLNHFMRPBPULJ-VKHMYHEASA-N;
	SMILES L:C1[C@H](NCS1)C(=O)O; zitteranion:C1[C@H]([NH2+]CS1)C(=O)[O-];
Properties
Chemical formula	C4H7NO2S
Molar mass	133.17 g·mol−1
Appearance	white solid
Density	1.578 g/cm3
Melting point	196.5 °C (385.7 °F; 469.6 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H312, H315, H319, H332, H335
Precautionary statements	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). Infobox references

Last updated April 13, 2025

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

↑ 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.

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[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 (1): 200–206. Bibcode:1937JAChS..59..200R. 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.

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[2]

[3]

[4]

[5]

Names

Other names (R)-1,3-Thiazolidin-3-ium-4-carboxylate
Identifiers
CAS Number	444-27-9 L: 34592-47-7
3D model (JSmol)	L: Interactive image zitteranion: Interactive image
Abbreviations	H-Thz-OH
ChEBI	L: CHEBI:45171
ChEMBL	L: ChEMBL1235440
ChemSpider	L: 84120
DrugBank	DB02846
ECHA InfoCard	100.047.355
EC Number	L:256-240-3
PubChem CID	L: 93176 zitteranion: 6973609
UNII	L: KL096K0KXL
CompTox Dashboard (EPA)	DTXSID3046536
InChI L:InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1 Key: DZLNHFMRPBPULJ-VKHMYHEASA-N
SMILES L:C1[C@H](NCS1)C(=O)O zitteranion:C1[C@H]([NH2+]CS1)C(=O)[O-]
Properties
Chemical formula	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]
Pictograms
Signal word	Danger
Hazard statements	H301, H312, H315, H319, H332, H335
Precautionary statements	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). Infobox references