65126-70-7

Usage

Uses

Used in Pharmaceutical Synthesis:
Thiazolidine-2-carboxylic acid is used as a key intermediate in the synthesis of azabicycloadducts and 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates). These compounds have potential applications in the development of new drugs and therapeutic agents, particularly in the treatment of various diseases and medical conditions.
Used in Chemical Research:
In the field of chemical research, Thiazolidine-2-carboxylic acid serves as a valuable building block for the creation of novel chemical entities. Its unique structure allows for the exploration of new chemical reactions and the development of innovative synthetic pathways, contributing to the advancement of organic chemistry and related disciplines.

Upstream product

• 20461-86-3 2,2-diethoxy acetic acid 
• 60-23-1 Cysteamine 
• 298-12-4 Glyoxilic acid 
• 156-57-0 2-mercaptoethylamine hydrochloride 

Downstream Products

• 916448-17-4 3-nitrosothiazolidin-2-carboxylic acid 

Relevant academic research and scientific papers

BIOCONJUGATION OF POLYPEPTIDES

Certain embodiments of the present invention relate to methods of forming and manipulating bioconjugates. Particularly, but not exclusively certain embodiments relate to methods of reversible carbon-carbon bond bioconjugation using aldol based chemical reactions at physiological conditions.

Palladium-unleashed proteins: Gentle aldehyde decaging for site-selective protein modification

Protein bioconjugation frequently makes use of aldehydes as reactive handles, with methods for their installation being highly valued. Here a new, powerful strategy to unmask a reactive protein aldehyde is presented. A genetically encoded caged glyoxyl aldehyde, situated in solvent-accessible locations, can be rapidly decaged through treatment with just one equivalent of allylpalladium(ii) chloride dimer at physiological pH. The protein aldehyde can undergo subsequent oxime ligation for site-selective protein modification. Quick yet mild conditions, orthogonality and powerful exposed reactivity make this strategy of great potential in protein modification.

Thiazolidine-Masked α-Oxo Aldehyde Functionality for Peptide and Protein Modification

α-Oxo aldehyde-based bioconjugation chemistry has been widely explored in peptide and protein modifications for various applications in biomedical research during the past decades. The generation of α-oxo aldehyde via sodium periodate oxidation is usually limited to the N-terminus of a target protein. Internal-site functionalization of proteins with the α-oxo aldehyde handle has not been achieved yet. Herein we report a novel method for site-specific peptide and protein modification using synthetically or genetically incorporated thiazolidine-protected α-oxo aldehyde. Efficient unmasking of the aldehyde was achieved by silver ion-mediated hydrolysis of thiazolidine under mild conditions for the first time. A model peptide and a recombinant protein were used to demonstrate the utility of this new method, which were site-specifically modified by oxime ligation with an oxyamine-functionalized peptide labeling reagent. Therefore, our current method has enriched the α-oxo aldehyde synthetic tool box in peptide and protein bioconjugation chemistry and holds great potential to be explored in novel applications in the future.

Anti-heparin peptides

The invention concerns a compound exhibiting an anti-heparin activity, of formula Z Bm ! (AXA)x Bn ! (AXA)y Bo (AXA)z Bp, the diagnostic reagents comprising it and the use of said compound in an in vitro diagnostic test of a medicine for anti-heparin activity.

Identification and quantitation of key aroma compounds formed in Maillard-type reactions of fructose with cysteamine or isothiaproline (1,3-thiazolidine-2-carboxylic acid)

Fructose was reacted in the presence of either cysteamine (model A) or isothiaproline (model B) in aqueous buffer at 145 °C and pH 7.0. Application of an aroma extract dilution analysis on the bulk of the volatile compounds formed in model A revealed 5-acetyl-3,4-dihydro-2H-1,4-thiazine (19), N-(2- mercaptoethyl)-1,3-thiazolidine (16), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (15), and 2-acetyl-2- thiazoline (11) as the key aroma compounds among the 10 odorants detected. A similar set of aroma compounds was formed when isothiaproline was reacted (model B), but the flavor dilution factors were generally lower. Substitution of the buffer by silica gel/water (9 + 1 w/w) in both models and application of 150 °C for 10 min also gave the same key odorants from both thio compounds; however, under these conditions isothiaproline was the better precursor of, in particular, 19 and 11. Quantitative measurements performed by means of stable isotope dilution assays revealed a significant effect of the pH on odorant formation. For example, in model A, formation of 19 as well as of 11 was suppressed at pH values 5.0. A clear maximum was, however, found for 19 at pH 7.0 (～1 mol % yield), whereas 11 increased with increasing pH from 7.0 to 9.0.

Spiro[pyrrolidine-2,3'-oxindole] compounds and methods of use

The invention provides spiro[pyrrolidine-2,3'-oxindole] compounds produced by the stereo- and regio-selective reaction of variously substituted isatins, alpha -amino acids, and dipolarophiles (e.g., trans-chalcones, acrylate esters, or vinyl oxindoles).

Preparation of optically active 2-thiazolidinecarboxylic acid by asymmetric transformation

Cysteamine was condensed with glyoxylic acid monohydrate in a mixture of acetic acid and ethanol in the presence of (2R,3R)- or (2S,3S)-tartaric acid [(R)- or (S)-TA], as the resolving agent, to give the salt of (-)-2- thiazolidinecarboxylic acid [(-)-2-THC] with (R)-TA or the salt of (+)-2-THC with (S)-TA. Treatment of these salts with triethylamine in methanol afforded (-)- and (+)-2-THC. The (-)- and (+)- 2-THC obtained were determined to be enantiopure forms by comparing their powder X-ray diffraction patterns with that of (RS)-2-THC. The absolute configurations of (-)- and (+)-2-THC were estimated based on molar rotations of (2R,4R)- and (2S,4R)-2,4- thiazolidinedicarboxylic acids, (R)-4-thiazolidinecarboxylic acid, and (-)- and (+)-2-THC. ()-2THC was determined to have the (R)-configuration, and (+)- 2-THC to have the (S)-configuration.

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

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 analogues thiazolidin

Fungicidal 6-(3,5-dichlorophenyl)perhydroimidazo[5,1-b]thiazole derivatives

This invention relates to fungicidal novel derivatives of 6-(3,5-dichlorophenyl)perhydroimidazo[5,1-b]thiazole derivative. These compounds may be used for controlling fungal infection, especially in agriculture.