67089-92-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2,2-DIMETHYL 4-THIAZOLIDINECARBOXYLIC ACID HYDROCHLORIDE is used as a key intermediate in the synthesis of complex organic molecules for pharmaceutical applications. Its chiral nature allows for the creation of enantiomerically pure compounds, which are essential in the development of drugs with improved efficacy and reduced side effects.
Used in Insect Kinin Core Pentapeptide Analogs:
(R)-2,2-DIMETHYL 4-THIAZOLIDINECARBOXYLIC ACID HYDROCHLORIDE is used as a building block for the preparation of pseudoproline-containing analogs of insect kinin core pentapeptide. These analogs have potential applications in the field of insect physiology and pest control, as they can modulate insect behavior and development.
Used in Cysteine-Derived Diketopiperazines:
(R)-2,2-DIMETHYL 4-THIAZOLIDINECARBOXYLIC ACID HYDROCHLORIDE is also utilized in the synthesis of cysteine-derived diketopiperazines. Diketopiperazines are cyclic dipeptides that exhibit a range of biological activities, including antimicrobial, anticancer, and immunosuppressive properties. The chiral thiazolidine compound contributes to the development of novel diketopiperazines with enhanced biological profiles and potential therapeutic applications.

Upstream product

• 52-89-1 l-cysteine hydrochloride 
• 67-64-1 acetone 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 869002-29-9 N-benzyloxycarbonylglycyl-L-4-thia-5,5-dimethylproline 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 917252-91-6 R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylic acid 
• 55878-44-9 L-4-carboxy-3-formyl-2,2-dimethylthiazolidine 
• 1212-53-9 methyl N-benzyloxycarbonylglycinate 
• 57704-00-4 3-benzoyl-2,2-dimethylthiazolidine-4R-carboxylic acid 
• 917253-02-2 pentafluorophenyl R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylate 
• 917252-97-2 pentafluorophenyl R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-D-valinyl)tetrahydrothiazole-4-carboxylate 
• 917253-01-1 pentafluorophenyl R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-valinyl)tetrahydrothiazole-4-carboxylate 
• 917253-06-6 R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 
• 917253-00-0 pentafluorophenyl R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-alanyl)tetrahydrothiazole-4-carboxylate 
• 917252-92-7 pentafluorophenyl R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)glycyl)tetrahydrothiazole-4-carboxylate 
• 917253-05-5 R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-valinyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 
• 917253-04-4 R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-alanyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide 

Relevant academic research and scientific papers

Conversion of L-cysteine into D-α-amino acids and related transformations

Naturally configured cysteine is converted into 4-substituted thiazolidines via the 4-carbaldehyde corresponding to the serine derived Garner's aldehyde. The key transformation is the conversion into 5-thiazolidinones by 1O2 oxidatio

A Short stereoselective synthesis of prepiscibactin using a SmI2-mediated reformatsky reaction and zn2+-induced asymmetric thiazolidine formation

Prepiscibactin (1) is a possible intermediate in the biosynthesis of piscibactin, the siderophore responsible for the iron uptake of the bacterium Photobacterium damselae subsp. piscicida, the aethiological agent of fish pasteurellosis. Compound 1 was syn

Rapid and specific post-synthesis modification of DNA through a biocompatible condensation of 1,2-aminothiols with 2-cyanobenzothiazole

Post-synthesis modification of DNA is an important way of functionalizing DNA molecules. Herein, we describe a method that first enzymatically incorporates a cyanobenzothiazole (CBT)-modified thymidine. The side-chain handle CBT can undergo a rapid and site-specific cyclization reaction with 1,2-aminothiols to afford DNA functionalization in aqueous solution. Another key advantage of this method is the formation of a single stereo/regioisomer in the process, which allows for precise control of DNA modification to yield a single component for aptamer selection work and other applications. The first enzymatic incorporation of a cyanobenzothiazole (CBT)-modified thymidine has been developed. The side-chain handle CBT can undergo a rapid and site-specific cyclization reaction with 1,2-aminothiols to enable DNA functionalization in aqueous solution. A key advantage of this method is the formation of a single stereo/regioisomer in the process, which allows for precise control of DNA modification to yield a single component (see scheme). Copyright

Memory of chirality in the electrochemical oxidation of thiazolidine-4-carboxylic acid derivatives

Memory of chirality in the electrochemical oxidation of thiazolidine-4-carboxylic acid derivatives was observed. The relatively larger size of sulphur atom than the oxygen atom for oxazolidine-4-carboxylic acid derivative may slightly improved the enantioselectivities of the oxidized products. The bulkier penicillamine derivative 1c furnished 2c with much better enantioselectivity (91% ee) than that of the cysteine derivative 2b (85% ee). The presence of two extra dimethyl groups, for the penicillamine derivative improved the enantioselectivities of the thiazolidine derivatives from 85% ee to 91 % ee.

Decoration of Au and Ag nanoparticles on self-assembling pseudopeptide-based nanofiber by using a short peptide as capping agent for metal nanoparticles

The surface of a nanofiber that is formed from a self-assembling pseudopeptlde has been decorated by gold and silver nanoparticles that are stabilized by a dipeptide. Transmission electron microscopic images make the decoration visible. In this paper, a new strategy of mineralizing a pseudopeptide based nanofiber by gold and silver nanoparticles with use of a two-component nanografting method is described.

Effects of steric bulk and stereochemistry on the rates of?diketopiperazine formation from N-aminoacyl-2,2-dimethylthiazolidine-4-carboxamides (Dmt dipeptide amides)-a model for a new prodrug linker system

A peptide-like self-immolative molecular clip is required for release of active drugs from prodrugs by endopeptidases. Upon cleavage from the carrier, this clip must collapse and release the drug rapidly. A series of aminoacyl-5,5-dimethylthiaproline (Aaa

Synthesis of proline-modified analogues of the neuroprotective agent glycyl-L-prolyl-glutamic acid (GPE)

The synthesis of ten proline-modified analogues of the neuroprotective tripeptide GPE is described. Five of the analogues incorporate a proline residue with a hydrophobic group at C-2 and two further analogues have this side chain locked into a spirolactam ring system. The pyrrolidine ring was also modified by replacing the γ-CH2 group with sulfur and/or incorporation of two methyl groups at C-5.

Boc-L-Dmt-OH as a Fully N,S-Blocked Cysteine Derivative for Peptide Synthesis by Prior Thiol Capture. Facile Conversion of N-Terminal Boc-L-Dmt-Peptides to H-Cys(Scm)-Peptides

An efficient, convenient preparation of N-L-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carboxylic acid (Boc-Dmt-OH) is reported.The following rate constants assess the coupling efficiency and racemization risk of Boc-L-Dmt-OC6F5 in THF at 22 deg C.With H-Val-OMe, kcouple = 3.2*10-2M-1s-1, and with Et3N, krac -8M-1s-1.Conversions of derivatives of the sequence Cys-Gly-Gly-Ala to the corresponding Scm-functionalized (Scm = methoxycarbonylsulfenyl, MeOCOS) cysteine peptides illustrated transformation of -Dmt- to -Cys(Scm)- with or without prior Boc cleavage.A palladium black catalyzed hydrogenolysis of a benzyl ester in the presence of the thiazolidine is reported in the solution-phase synthesis of the tripeptide Boc-Dmt-Leu-Ala-OBzl.The functionalized octapeptide 58-51 of basic pancreatic trypsin inhibitor, H-Cys(Scm)-Met-Arg-Thr-Cys(Dnp)-Gly-Gly-Ala-OH, was prepared by a 4 + 4 thiol capture and acyl-transfer strategy to demonstrate the applicability of the thiazolidine to this method.