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

Chemical Properties

White Solid

Uses

Found to act on the cell membrane of tumour cells, possible causing a reverse transformation to normal cells through restoration of contact inhibition.

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 
• 85929-61-9 methyl (+/-)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 
• 52-66-4 DL-Penicillamin 

Downstream Products

• 117918-23-7 (tert-butyloxycarbonyl)-L-5,5-dimethylthiazolidine-4-carboxylic acid 
• 1303947-82-1 KNI-10859 
• 1303947-75-2 KNI-10857 
• 1303947-72-9 KNI-10838 
• 1303947-68-3 KNI-10856 
• 1303947-64-9 KNI-10605 
• 1303947-59-2 KNI-10608 
• 1248544-12-8 KNI-10562 
• 1303947-94-5 KNI-10756 
• 1303947-92-3 KNI-10767 

Relevant articles and documents

α-Substituted norstatines as the transition-state mimic in inhibitors of multiple digestive vacuole malaria aspartic proteases

The impact of moving the P1 side-chain from the β-position to the α-position in norstatine-containing plasmepsin inhibitors was investigated, generating two new classes of tertiary alcohol-comprising α-benzylnorstatines and α-phenylnorstatines. Twelve α-s

Multimeric VLA-4 antagonists comprising polymer moieties

Disclosed are conjugates which bind VLA-4. Certain of these conjugates also inhibit leukocyte adhesion and, in particular, leukocyte adhesion mediated by VLA-4. Such conjugates are useful in the treatment of inflammatory diseases in a mammalian patient, e.g., human, such as asthma, Alzheimer's disease, atherosclerosis, AIDS dementia, diabetes, inflammatory bowel disease, rheumatoid arthritis, tissue transplantation, tumor metastasis and myocardial ischemia. The conjugates can also be administered for the treatment of inflammatory brain diseases such as multiple sclerosis.

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.