Thiazolidine Chemistry. II. The Preparation of 2-Substituted Thiazolidine-4-carboxylic Acids^1,2

Antioxidant effect of thiazolidine molecules in cell culture media improves stability and performance

“…In general, thiazolidines are formed from the reaction of cysteine with aldehydes or ketoacids . The amount of potential condensation partners is tremendous and includes several aliphatic and aromatic aldehydes, sugars like N ‐acetyl‐glucosamine, arabinose, ribose, xylose, galactose, glucose or mannose, or activated vitamins like pyridoxal phosphate . 2‐Methyl‐1,3‐thiazolidine‐2,4‐dicarboxylic acid (CP) is probably the most studied molecule with data available on its kinetics of formation and hydrolysis …”

“…This study describes the use of thiazolidines, formed by cyclo‐condensation between l ‐cysteine and α‐ketoacids to protect cell culture media from RS‐induced degradation. The benefits of using these molecules to improve the productivity of clinically relevant monoclonal antibodies in Chinese hamster ovary (CHO) cells are also described.…”

“…24,25 Furthermore, pyruvate has been shown to preserve free sulfhydryls in media incubated at 378C 23 whereas a-KG was able to react with amino groups, thus leading to decreased ammonia levels. 26 This study describes the use of thiazolidines, formed by cyclo-condensation between L-cysteine and a-ketoacids 27,28 to protect cell culture media from RS-induced degradation. The benefits of using these molecules to improve the productivity of clinically relevant monoclonal antibodies in Chinese hamster ovary (CHO) cells are also described.…”

Synthesis and biological activity of pyochelin, a siderophore of Pseudomonas aeruginosa

“…L-N-Methylcysteine was prepared as its monohydrochloride (compound 6) by the method of Blondeau et al (6) 4. After removal of the solvent from the thexylborane reduction mixture, the residue was suspended in ethanol and subjected to condensation with L-N-methylcysteine (compound 6), using the standard method of thiazolidine formation (36). The condensation reaction mixture was added to 200 ml of 10 mM KH2PO4-acetic acid (pH 3.0) and was extracted twice with 200-ml volumes of CH2Cl2.…”

Combining a flow reactor with spray dryer to allow the preparation of food-grade quality sodium 2-polyhydroxyalkyl-1,3-thiazolidine-4-carboxylates with a low environmental impact

“…The 1,3-thiazolidine-4-carboxylic acid (TCA) and 2-substituted 1,3-thiazolidine-4-carboxylic acids (2S-TCAs) prepared from the condensation of cysteine and aldehydes have been studied extensively. [1][2][3][4] The formation of a thiazolidine ring results from hemimercaptal formation from aldehydes on cysteine, followed by dehydration and cyclization. These compounds can be used as prodrugs of L-cysteine, which can release the sulydryl amino acid and the corresponding aldehyde compound by non-enzymatic ring-opening hydrolysis.…”