5874-58-8

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

• 98-88-4 benzoyl chloride 
• 147-85-3 L-proline 
• 92010-20-3 (S)-1-benzoyl-pyrrolidine-2-carboxylic acid benzyl ester 
• 609-36-9 rac-Pro-OH 
• 2812-46-6 proline tert-butyl ester 
• 195719-48-3 N-benzoylproline 
• 1523-16-6 2,6-dinitrophenyl benzoate 
• 1694-28-6 2,5-dinitrophenyl benzoate 
• 1523-15-5 2,4-dinitrophenyl benzoate 
• 58156-44-8 2,4,6-trinitrophenyl benzoate 
• 959-22-8 p-nitrophenylbenzoate 
• 23405-15-4 benzoic acid N-hydroxysuccinimide ester 
• 65-85-0 benzoic acid 
• 1523-13-3 3-nitrophenyl benzoate 

Downstream Products

• 5493-38-9 N-benzoyl-L-proline methyl ester 
• 133392-33-3 (S)-1-Benzoyl-pyrrolidine-2-carboxylic acid 1-phenyl-ethyl ester 
• 118459-72-6 (-)-N-benzoyl-L-prolyl-L-phenylalanine methyl ester 
• 92010-21-4 (S)-1-Benzoyl-pyrrolidine-2-carboxylic acid 2-benzyloxycarbonyl-phenyl ester 
• 124731-68-6 (-)-N-benzoyl-L-prolyl-D-phenylalanine methyl ester 
• 78867-94-4 N-benzoyl-L-prolyl-L-valine methyl ester 
• 88105-62-8 N-benzoyl-L-prolyl-L-phenylalanine benzyl ester 
• 144317-07-7 Bz-Pro-Ser-OMe 
• 1027016-69-8 C₁₇H₂₁NO₅ 
• 53912-80-4 (S)-N-benzylprolinol 
• 137521-24-5 4-(benzoylamino)butanal 
• 96133-48-1 (2-hydroxypyrrolidin-1-yl) (phenyl)methanone 

Relevant academic research and scientific papers

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.

Reactivity of Tyrosyl–Proline toward Benzoylation in Aqueous 1,4-Dioxane

Abstract: The kinetics of the reaction of L-tyrosyl-L-proline (Tyr–Pro) with di- andtrinitrophenyl benzoates in aqueous 1,4-dioxane (40 wt percent of water) were studiedin the temperature range 298–313 K. The reaction rate constant k298 was fou

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.

Retention of chirality of 5-membered alicyclic α-amino acids bearing N-(2-phenyl)benzoyl group in photoinduced decarboxylative intermolecular radical addition to acrylonitrile

Photoinduced decarboxylative radical additions of 5-membered alicyclic α-amino acids bearing a (2-phenyl)benzoyl protective group to acrylonitrile under mild organic photoredox catalysis conditions furnished γ-amino acid derivatives with high retention of chirality via the memory of chirality (MOC) strategy. The retention of chirality in the photoinduced decarboxylation was strongly dependent on the structure of the alicyclic α-amino acids and alkenes. To the best of our knowledge, this is the first example of the decarboxylative intermolecular radical addition to alkenes with retention of chirality at the position of radical generation using the MOC strategy.

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.

Reductive ipso-radical cyclization onto aromatic rings of five-membered alicyclic amino acids bearing N-(2-phenyl)benzoyl groups by photoinduced electron transfer promoted decarboxylation

A new radical cyclization has been developed for the one-step synthesis of spiro dihydroisoquinolinone derivatives from alicyclic amino acids bearing N-(2-phenyl)benzoyl groups through photoinduced electron transfer (PET)-promoted decarboxylation. Reductive ipso-radical cyclization onto a benzene ring by an alkyl radical is achieved under mild conditions for the first time, although the substrates are limited to five-membered aliphatic carboxylic acids bearing N-(2-phenyl)benzoyl groups.

Isotope-labeled differential profiling of metabolites using N-benzoyloxysuccinimide derivatization coupled to liquid chromatography/high-resolution tandem mass spectrometry

Rationale An isotopic labeling strategy based on derivatizing amine-containing metabolites has been developed using light (12C6) and heavy (13C6) N-benzoyloxysuccinimide reagents for semi-targeted metabolomic applications. Methods Differentially labeled samples were combined and analyzed simultaneously by liquid chromatography/high-resolution tandem mass spectrometry (LC/HR-MS/MS) to compare relative amounts of amine-containing metabolites. The selectivity of the reaction was determined with model metabolites and was shown to also be applicable to thiol and phenol moieties. The potential for relative quantitation was evaluated in cell extracts and the method was then applied to quantify metabolic perturbations occurring in human cultured cells under normal vs. oxidative stress conditions. Results A total of 279 derivatized features were detected in HL60 cell extracts, 77 of which yielded significant concentration changes upon oxidative stress treatment. Based on accurate mass measurements and MS/MS spectral matching with reference standard solutions, 10 metabolites were clearly identified. Derivatized compounds were found to have diagnostic fragment ions from the reagent itself, as well as structurally informative ions useful for metabolite identification. Conclusions This simple derivatization reaction can be applied to the relative quantitation of amine-, thiol- and phenol-containing compounds, with improved sensitivity and chromatographic peak shapes due to the increased hydrophobicity of polar metabolites not readily amenable to reversed-phase LC/MS analysis.

Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds

The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds. Strong as an ox: The highly chemoselective aerobic oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has been achieved by using 2-azaadamantane N-oxyl (AZADO)/copper catalysis. This catalytic system oxidizes not only alcohols with tertiary amino groups but also those with secondary and primary amines in good to high yield at ambient temperature in air. bpy=2,2-bipyridyl, DMAP=4-(N,N-dimethylamino)pyridine.

Cross aldol condensation of acetaldehyde and formaldehyde in the presence of bifunctional systems

Liquid-phase cross-aldol condensation of acetaldehyde and formaldehyde in the presence of salts of various saturated and unsaturated linear amines, aromatic amines, diamines, and nitrogen bases, as well as in the presence of substituted piperazines, linear and cyclic amino acids and their derivatives, and nitrogen-containing ionic liquids, was studied. The cross-condensation products were formed in considerable amounts when amine hydrochlorides, N-benzoyl amino acids, and amino acid esters were used as catalyst. The formation of cross-condensation products is favored by increased basicity of the amino nitrogen atom in the salt and of the solvent.

Asymmetric synthesis of (-)-(1R,7aS)-absouline

The most efficient and concise asymmetric synthesis of (-)-(1R,7aS)- absouline to date, which was accomplished in eight steps and 20% overall yield from commercially available starting materials, is described. The doubly diastereoselective conjugate addit