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467995

Sigma-Aldrich

Thiazolidine-2-carboxylic acid

97%

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About This Item

Formule empirique (notation de Hill):
C4H7NO2S
Numéro CAS:
65126-70-7
Poids moléculaire :
133.17
Numéro MDL:
MFCD00068005
Code UNSPSC :
12352100
ID de substance PubChem :
24870454
Nomenclature NACRES :
NA.22

Pureté

97%

Pf

176 °C (lit.)

Chaîne SMILES 

OC(=O)C1NCCS1

InChI

1S/C4H7NO2S/c6-4(7)3-5-1-2-8-3/h3,5H,1-2H2,(H,6,7)

Clé InChI

ULSZVNJBVJWEJE-UHFFFAOYSA-N

Description générale

Thiazolidine-2-carboxylic acid (β-thiaproline) is a proline analog. It is an important building block of β-lactam antibiotics. Its X-ray photoelectron spectra has been investigated. It has been reported as a physiological substrate of hog kidney D-amino acid oxidase. Thiazolidine-2-carboxylic acid can be synthesized from cysteamine and glyoxylate.

Application

Thiazolidine-2-carboxylic acid may be used in the synthesis of azabicycloadducts and 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates).

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Classification des risques

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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V Busiello et al.
Biochimica et biophysica acta, 564(2), 311-321 (1979-09-27)
Thiazolidine-2-carboxylic acid, or beta-thiaproline, is a proline analog in which the beta methylene group of proline is substituted by a sulfur atom. It has been deomonstrated that beta-thiaproline is activated and transferred to tRNAPro by Escherichia coli and rat liver
L Włodek et al.
Biochemical pharmacology, 46(1), 190-193 (1993-07-06)
2-Substituted thiazolidine-4(R)-carboxylic acids (TD) were found to increase the concentration of non-protein sulphydryls (NPSH) and the activity of rhodanese (thiosulphate sulphurtransferase, EC 2.8.1.1) and 3-mercaptopyruvate sulphurtransferase (EC 2.8.1.2) in mouse liver. These properties suggest TDs are potentially hepatoprotective compounds. However
C L Burns et al.
Biochemical and biophysical research communications, 125(3), 1039-1045 (1984-12-28)
Adducts of glyoxylate with L-cysteine or L-cysteinylglycine were found to be excellent substrates at low concentrations for beef kidney D-aspartate oxidase. Evidence is presented that cis-thiazolidine-2,4-dicarboxylate and its glycine amide are the actual substrates, and that both are converted in
Synthesis and chromatographic properties of selenazolidine-2-carboxylic acid (beta-selenaproline).
C De Marco et al.
The Italian journal of biochemistry, 28(2), 104-110 (1979-03-01)
C Foppoli et al.
The Italian journal of biochemistry, 30(5), 355-366 (1981-09-01)
Beta-DL-Thiaproline (thiazolidine 2-carboxylic acid) is a good substrate for hog kidney D-aminoacid oxidase. Unlike other known substrates, beta-thiaproline is better oxidized at neutral than at alkaline pH. At neutral pH beta-thiaproline is a better substrate than D-proline. Beta-DL-thiaproline is fully
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