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467995

Sigma-Aldrich

Thiazolidine-2-carboxylic acid

97%

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About This Item

Empirical Formula (Hill Notation):
C4H7NO2S
CAS Number:
65126-70-7
Molecular Weight:
133.17
MDL number:
MFCD00068005
UNSPSC Code:
12352100
PubChem Substance ID:
24870454
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

176 °C (lit.)

SMILES string

OC(=O)C1NCCS1

InChI

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

InChI key

ULSZVNJBVJWEJE-UHFFFAOYSA-N

General description

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).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4464
MKCS0311
MKCP5124
MKCL8352
MKCK4954

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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)
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
I Lalezari et al.
Journal of medicinal chemistry, 31(7), 1427-1429 (1988-07-01)
A series of 1-thia analogues of the pyrrolizine bis(carbamate) 9 (NSC-278214), namely 5-aryl-2,3-dihydropyrrolo-[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates) (7a-d), were prepared by multistep syntheses from the proline analogue thiazolidine-2-carboxylic acid. The compounds were tested for growth inhibitory activity with the HL-60 human promyelocytic leukemia
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