Thiazolidine-2-carboxylic acid

Name: Thiazolidine-2-carboxylic acid
Brand: ALDRICH

97%

Slide 1 of 1

Select a Size

Pricing and availability is not currently available.

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

Key Documents

View All Documentation

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

Related Categories

Chemical Building Blocks

Heterocyclic Building Blocks

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item	328464	251089	512362
Sigma-Aldrich 467995 Thiazolidine-2-carboxylic acid	Sigma-Aldrich 328464 2-Azetidinone	Sigma-Aldrich 251089 2-(Methylthio)pyridine-3-carboxylic acid	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

GHS07

signalword

Warning

hcodes

H302 + H312 + H332,H315,H319,H335

pcodes

P261 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Thiazolidine-2-carboxylic acid, an adduct of cysteamine and glyoxylate, as a substrate for D-amino acid oxidase.

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.

[3 + 2] Cycloaddition reactions of thioisatin with thiazolidine-2-carboxylic acid: a versatile route to new heterocyclic scaffolds.

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

Synthesis and antineoplastic activity of 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates).

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

Action of thiazolidine-2-carboxylic acid, a proline analog, on protein synthesizing systems.

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

Thiazolidine-2-carboxylate derivatives formed from glyoxylate and L-cysteine or L-cysteinylglycine as possible physiological substrates for D-aspartate oxidase.

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

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.

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service