72778-00-8

Basic information

• Product Name: L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID
• Synonyms: L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID;(R)-5,5-DIMETHYL-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID;(R)-DTC-OH;(R)-5,5-Dimethyl-4-thiazolidinecarboxylic Acid;L-5,5-Dimethylthiazolidine-4-carboxyl;(R)-4-Carboxy-5,5-dimethylthiazolidine;(R)-5,5-Dimethylthiazolidine-4-carboxylic acid
• CAS NO: 72778-00-8
• Molecular Formula: C₆H₁₁NO₂S
• Molecular Weight: 161.22
• Product Categories: All Inhibitors;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;A - H;Amino Acids;Modified Amino Acids
• Mol File: 72778-00-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 206°C dec.
• Appearance: /
• Refractive Index: [a]20D = - 149 ± 2 o (C=1 in water)
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane, DMSO, Methanol
• CAS DataBase Reference: L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID(72778-00-8)
• EPA Substance Registry System: L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID(72778-00-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 72778-00-8(Hazardous Substances Data)

Usage

Description

L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID is an organic compound with the chemical formula C7H11NO4S. It is a chiral molecule with a unique structure that includes a thiazolidine ring and a carboxylic acid group. L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID has potential applications in various fields due to its chemical properties and biological activity.

Uses

Used in Pharmaceutical Industry:
L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure and chirality make it a valuable building block in the development of new therapeutic agents.
Used in Anticancer Applications:
L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID is used as an anticancer agent for its potential to act on the cell membrane of tumor cells. It may cause a reverse transformation to normal cells through the restoration of contact inhibition, offering a novel approach to cancer treatment.
Used in Drug Delivery Systems:
L-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID can be used in the development of drug delivery systems to improve the bioavailability and therapeutic efficacy of various drugs. Its unique structure and properties may allow for the design of targeted drug delivery systems, enhancing the treatment of specific diseases.

Biological Activity

L-5,5-Dimethylthiazolidine-4-carboxylic acid (DTC) is used as a proline analog with restricted conformation in studies on receptor bound conformational requirements for agonists and antagonists of angiotensin II (ANG II).

Upstream product

• 50-00-0 formaldehyd 
• 1113-41-3 L-penicillamine 
• 52-66-4 DL-Penicillamin 
• 85929-61-9 methyl (+/-)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 

Downstream Products

• 117918-23-7 (tert-butyloxycarbonyl)-L-5,5-dimethylthiazolidine-4-carboxylic acid 
• 117918-23-7 (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 
• 220545-25-5 N-(1-methylpyrazole-4-sulfonyl)-L-(5,5-dimethyl)thiaprolyl-L-4-(N,N-dimethylcarbamyloxy)phenylalanine 
• 220545-48-2 N-(1-methylpyrazole-4-sulfonyl)-L-(5,5-dimethyl)thiaprolyl-L-4-(N,N-dimethylcarbamyloxy)phenylalanine isopropyl ester 
• 220545-24-4 N-(1-methylpyrazole-4-sulfonyl)-L-(5,5-dimethyl)thiaprolyl-L-4-(N,N-dimethylcarbamyloxy)phenylalanine tert-butyl ester 
• 321435-39-6 (R)-3-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carbonyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid 
• 321435-38-5 (R)-3-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carbonyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid allyl ester 
• 321435-43-2 (R)-3-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carbonyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid (3-methyl-pyridin-2-ylmethyl)-amide 
• 321435-45-4 (R)-3-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carbonyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide 
• 321435-40-9 (R)-3-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carbonyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,6-dimethyl-benzylamide 
• 588729-42-4 (R)-3-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carbonyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid (2,4-dimethyl-pyridin-3-ylmethyl)-amide 
• 627893-96-3 (R)-3-((2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carbonyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isothiazol-4-ylmethyl)-amide 

Relevant articles and documents

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A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an α-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (±)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (±)-8b in 46% yield for another round of the enzymatic processing.