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Merck

467995

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
NACRES:
NA.22
PubChem Substance ID:
24870454
UNSPSC Code:
12352100
MDL number:
MFCD00068005

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Product Name

Thiazolidine-2-carboxylic acid, 97%

InChI

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

SMILES string

OC(=O)C1NCCS1

InChI key

ULSZVNJBVJWEJE-UHFFFAOYSA-N

assay

97%

mp

176 °C (lit.)

functional group

carboxylic acid
thioether

Quality Level

100

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1 of 4

This Item
328464251089512362
Thiazolidine-2-carboxylic acid 97%

Sigma-Aldrich

467995

Thiazolidine-2-carboxylic acid

2-Azetidinone 98%

Sigma-Aldrich

328464

2-Azetidinone

2-(Methylthio)pyridine-3-carboxylic acid 98%

Sigma-Aldrich

251089

2-(Methylthio)pyridine-3-carboxylic acid

3-Methylpyridine-2-carboxylic acid 97%

Sigma-Aldrich

512362

3-Methylpyridine-2-carboxylic acid

assay

97%

assay

98%

assay

98%

assay

97%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

176 °C (lit.)

mp

74-76 °C (lit.)

mp

215-217 °C (lit.)

mp

114-118 °C

functional group

carboxylic acid

functional group

-

functional group

carboxylic acid, thioether

functional group

carboxylic acid

Application

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

General description

Thiazolidine-2-carboxylic acid (β-thiaproline) is a proline analog.[3] It is an important building block of β-lactam antibiotics. Its X-ray photoelectron spectra has been investigated.[4] 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.[5]

pictograms

Exclamation mark
GHS07

signalword

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ8414
MKCZ1825
MKCW4464
MKCS0311
MKCP5124

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Inhibition of dopamine beta-hydroxylase by thiazoline-2-carboxylate, a suspected physiological product of D-amino acid oxidase.
N Naber et al.
Biochemical and biophysical research communications, 107(1), 374-380 (1982-07-16)
P F Fitzpatrick et al.
The Journal of biological chemistry, 257(3), 1166-1171 (1982-02-10)
A mixture of cysteamine and glyoxylate, proposed by Hamilton et al. to form the physiological substrate of hog kidney D-amino acid oxidase (Hamilton, G. A., Buckthal, D. J., Mortensen, R. M., and Zerby, K. W. (1979) Proc. Natl. Acad. Sci.
Sonali Verma et al.
Organic and medicinal chemistry letters, 1(1), 6-6 (2012-03-01)
A facile synthesis of azabicycloadducts is described by 1,3-dipolar cycloaddition reactions of thioisatin with thiazolidine-2-carboxylic acid in the presence of various electron rich and electron deficient dipolarophiles. Theoritical calculations have been performed to study the regioselectivity of products. The geometrical
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
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
View All Related Papers

Articles

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.

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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