5874-58-8

Basic information

• Product Name: N-Benzoyl-L-proline
• Synonyms: N-Benzoyl-L-proline;(S)-1-benzoylpyrrolidine-2-carboxylic acid
• CAS NO: 5874-58-8
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• Product Categories: pharmacetical
• Mol File: 5874-58-8.mol
• Article Data: 31

Chemical Properties

• Melting Point: 153-155 °C(Solv: hexane (110-54-3))
• Boiling Point: 428.9°Cat760mmHg
• Flash Point: 213.2°C
• Appearance: /
• Density: 1.296g/cm³
• Vapor Pressure: 4.05E-08mmHg at 25°C
• Refractive Index: 1.599
• PKA: 5.30±0.10(Predicted)
• CAS DataBase Reference: N-Benzoyl-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzoyl-L-proline(5874-58-8)
• EPA Substance Registry System: N-Benzoyl-L-proline(5874-58-8)

Safety Data

• Hazardous Substances Data: 5874-58-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H13NO3/c14-11(9-5-2-1-3-6-9)13-8-4-7-10(13)12(15)16/h1-3,5-6,10H,4,7-8H2,(H,15,16)/t10-/m0/s1

Upstream product

• 41324-66-7 H-Pro-OBzl 
• 93-99-2 benzoic acid phenyl ester 
• 147-85-3 L-proline 
• 1523-16-6 2,6-dinitrophenyl benzoate 
• 1523-13-3 3-nitrophenyl benzoate 
• 959-22-8 p-nitrophenylbenzoate 
• 58156-44-8 2,4,6-trinitrophenyl benzoate 
• 1694-28-6 2,5-dinitrophenyl benzoate 
• 1523-15-5 2,4-dinitrophenyl benzoate 
• 98-88-4 benzoyl chloride 
• 92010-20-3 (S)-1-benzoyl-pyrrolidine-2-carboxylic acid benzyl ester 
• 23405-15-4 benzoic acid N-hydroxysuccinimide ester 
• 65-85-0 benzoic acid 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 

Downstream Products

• 144317-07-7 Bz-Pro-Ser-OMe 
• 557790-57-5 1-benzoyl-2-(dimethylsulfuranylideneacetyl)pyrrolidine 

Relevant articles and documents

Identification of Novel Fragments Binding to the PDZ1-2 Domain of PSD-95

Inhibition of PSD-95 has emerged as a promising strategy for the treatment of ischemic stroke, as shown with peptide-based compounds that target the PDZ domains of PSD-95. In contrast, developing potent and drug-like small molecules against the PSD-95 PDZ domains has so far been unsuccessful. Here, we explore the druggability of the PSD-95 PDZ1-2 domain and use fragment screening to investigate if this protein is prone to binding small molecules. We screened 2500 fragments by fluorescence polarization (FP) and validated the hits by surface plasmon resonance (SPR), including an inhibition counter-test, and found four promising fragments. Three ligand efficient fragments were shown by 1H,15N HSQC NMR to bind in the small hydrophobic P0 pockets of PDZ1-2, and one of them underwent structure-activity relationship (SAR) studies. Overall, we demonstrate that fragment screening can successfully be applied to PDZ1-2 of PSD-95 and disclose novel fragments that can serve as starting points for optimization towards small-molecule PDZ domain inhibitors.

Memory of Chirality in Flow Electrochemistry: Fast Optimisation with DoE and Online 2D-HPLC

Amino acid derivatives undergo non-Kolbe electrolysis to afford enantiomerically enriched α-alkoxyamino derivatives through intermediate chiral carbenium ions. The products contain N,O-acetals which are important structural motifs found in bioactive natural products. The reaction is performed in a continuous flow electrochemical reactor coupled to a 2D-HPLC for immediate online analysis. This allowed a fast screening of temperature, electrode material, current, flow-rate and concentration in a DoE approach. The combination with online HPLC demonstrates that also stereoselective reactions can benefit from a hugely accelerated optimisation by combining flow electrochemistry with multidimensional analysis.

Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media

The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Br?nsted dependence and revealed linear correlation between rate constant logarithm and the energy difference of the frontier orbitals of α-amino acids anions.