168264-25-3

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 4-[(4-nitrobenzoyl)oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S-cis)-
• CAS NO: 168264-25-3
• Molecular Formula: C18H22N2O8
• Molecular Weight: 394.381
• Mol File: 168264-25-3.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[(4-nitrobenzoyl)oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S-cis)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[(4-nitrobenzoyl)oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S-cis)-(168264-25-3)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 4-[(4-nitrobenzoyl)oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S-cis)-(168264-25-3)

Safety Data

• Hazardous Substances Data: 168264-25-3(Hazardous Substances Data)

Usage

General Description

The chemical "1,2-Pyrrolidinedicarboxylic acid, 4-[(4-nitrobenzoyl)oxy]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S-cis)-" is a compound commonly known as taurine. It is a sulfur-containing amino acid that is found in high concentrations in the brain, heart, and muscles. Taurine is involved in various physiological processes, including bile salt formation, antioxidation, and the modulation of neurotransmitter activity. It has been used in various pharmaceutical and nutritional applications, including as a dietary supplement for its potential benefits on cardiovascular health and exercise performance. Additionally, taurine has been studied for its potential therapeutic effects on conditions such as diabetes, liver disease, and neurodegenerative disorders.

Upstream product

• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 1972-28-7 diethylazodicarboxylate 
• 62-23-7 4-nitro-benzoic acid 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 

Downstream Products

• 191280-88-3 (2S,4S)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 143035-54-5 C₆H₁₂N₂O₂ 
• 168264-26-4 (2S,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 168264-27-5 (2S,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 

Relevant articles and documents

The Distinct Conformational Landscapes of 4S-Substituted Prolines That Promote an endo Ring Pucker

4-Substitution on proline directly impacts protein main chain conformational preferences. The structural effects of N-acyl substitution and of 4-substitution were examined by NMR spectroscopy and X-ray crystallography on minimal molecules with a proline 4

Cross-Linked Collagen Triple Helices by Oxime Ligation

Covalent cross-links are crucial for the folding and stability of triple-helical collagen, the most abundant protein in nature. Cross-linking is also an attractive strategy for the development of synthetic collagen-based biocompatible materials. Nature uses interchain disulfide bridges to stabilize collagen trimers. However, their implementation into synthetic collagen is difficult and requires the replacement of the canonical amino acids (4R)-hydroxyproline and proline by cysteine or homocysteine, which reduces the preorganization and thereby stability of collagen triple helices. We therefore explored alternative covalent cross-links that allow for connecting triple-helical collagen via proline residues. Here, we present collagen model peptides that are cross-linked by oxime bonds between 4-aminooxyproline (Aop) and 4-oxoacetamidoproline placed in coplanar Xaa and Yaa positions of neighboring strands. The covalently connected strands folded into hyperstable collagen triple helices (Tm 80 °C). The design of the cross-links was guided by an analysis of the conformational properties of Aop, studies on the stability and functionalization of Aop-containing collagen triple helices, and molecular dynamics simulations. The studies also show that the aminooxy group exerts a stereoelectronic effect comparable to fluorine and introduce oxime ligation as a tool for the functionalization of synthetic collagen.

Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents

Ethyl 2-arylhydrazinecarboxylates can work as organocatalysts for Mitsunobu reactions because they provide ethyl 2-arylazocarboxylates through aerobic oxidation with a catalytic amount of iron phthalocyanine. First, ethyl 2-(3,4-dichlorophenyl)hydrazinecarboxylate has been identified as a potent catalyst, and the reactivity of the catalytic Mitsunobu reaction was improved through strict optimization of the reaction conditions. Investigation of the catalytic properties of ethyl 2-arylhydrazinecarboxylates and the corresponding azo forms led us to the discovery of a new catalyst, ethyl 2-(4-cyanophenyl)hydrazinecarboxylates, which expanded the scope of substrates. The mechanistic study of the Mitsunobu reaction with these new reagents strongly suggested the formation of betaine intermediates as in typical Mitsunobu reactions. The use of atmospheric oxygen as a sacrificial oxidative agent along with the iron catalyst is convenient and safe from the viewpoint of green chemistry. In addition, thermal analysis of the developed Mitsunobu reagents supports sufficient thermal stability compared with typical azo reagents such as diethyl azodicarboxylate (DEAD). The catalytic system realizes a substantial improvement of the Mitsunobu reaction and will be applicable to practical synthesis.