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467995

Sigma-Aldrich

Thiazolidin-2-carbonsäure

97%

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About This Item

Empirische Formel (Hill-System):
C4H7NO2S
CAS-Nummer:
65126-70-7
Molekulargewicht:
133.17
MDL-Nummer:
MFCD00068005
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24870454
NACRES:
NA.22

Assay

97%

mp (Schmelzpunkt)

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)

InChIKey

ULSZVNJBVJWEJE-UHFFFAOYSA-N

Allgemeine Beschreibung

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.

Anwendung

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).

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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
Fang Xie et al.
Journal of fluorescence, 28(1), 89-96 (2017-09-11)
Copper complexes with strong anticancer activity are promising new drugs for treatment of patients with metastatic cancer. Copper 8-hydroxyquinoline-2-carboxaldehyde-thiosemicarbazide (CuHQTS) and copper 8-hydroxyquinoline-2-carboxaldehyde-4,4-dimethyl-3-thiosemicarbazide (CuHQDMTS) were found to have strong anticancer activity against cisplatin-resistant neuroblastoma cells and prostate cancer cells. This
W M Frederiks et al.
The Histochemical journal, 25(8), 578-582 (1993-08-01)
D-Amino acid oxidase activity was demonstrated in peroxisomes of rat liver using unfixed cryostat sections and a histochemical technique using cerium ions as capture reagent for hydrogen peroxide and diaminobenzidine, cobalt ions and exogenous hydrogen peroxide to visualize the final
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
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
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Artikel

Proline Derivatives and Analogs

Proline analogues are promising candidates for tuning the biological, pharmaceutical, or physicochemical properties of naturally occuring, as well as de novo designed, linear, and, cyclic peptides.

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