31795-93-4

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzyl-L-Proline is used as a reagent for the synthesis of optically pure α-amino-acids, which are crucial building blocks for the development of various pharmaceuticals. Its ability to produce optically pure compounds ensures the desired biological activity and therapeutic effects of the final drug product.
Used in Bioactive Compounds Synthesis:
N-Benzyl-L-Proline is also used as a reagent in the synthesis of bioactive compounds, such as peptides, proteins, and other biologically relevant molecules. Its unique structure allows for the creation of novel compounds with potential applications in research, medicine, and other industries.

InChI:InChI=1/C12H15NO2/c14-12(15)11-7-4-8-13(11)9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,14,15)/t11-/m0/s1

Upstream product

• 100-44-7 benzyl chloride 
• 147-85-3 L-proline 
• 71989-31-6 Fmoc-Pro-OH 
• 100-52-7 benzaldehyde 
• 955-40-8 N-benzyl-L-proline ethyl ester 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 90741-31-4 (S)-N-benzyl-5-thioxoproline tert-butyl ester 
• 170642-58-7 (S)-N-benzylproline tert-butyl ester 
• 83528-04-5 (S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate 

Downstream Products

• 138052-86-5 (S)-1-(1-benzylpyrrolidin-2-yl)ethanone 
• 96293-17-3 (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide 
• 105099-19-2 N-benzyl-(S)-proline chloroanhydride 
• 92086-93-6 (S)-1-benzylpyrrolidine-2-carboxylic acid hydrochloride 
• 211805-51-5 (S)-1-Benzyl-pyrrolidine-2-carboxylic acid ((S)-1-benzyl-pyrrolidin-2-ylmethyl)-amide 
• 211805-57-1 (S)-1-Benzyl-pyrrolidine-2-carboxylic acid bis-((S)-1-benzyl-pyrrolidin-2-ylmethyl)-amide 
• 384333-96-4 N,N'-bis[2(S)-2-pyrrolidinylmethyl]phenylenediamine 
• 479677-97-9 N,N'-bis[(S)-N-benzylprolyl]-N-(2-aminoethyl-3-aminopropyl)triethoxysilylethylenediamine 
• 211805-54-8 N,N-bis([(S)-1-benzylpyrrolidin-2-yl]methyl)amine 
• 211805-60-6 Tris-((S)-1-benzyl-pyrrolidin-2-ylmethyl)-amine 
• 96948-23-1 1-[(2S)-N-Benzylpyrrolidin-2-yl]methanamine 
• 205388-64-3 (2S)-2-(1-Oxo-4-phenyl)butyl-N-benzylpyrrolidine 
• 193345-58-3 N-{4-(2-Amino-4-thiazolyl)phenyl}-1-(phenylmethyl)-2 (S)-pyrrolidinecarboxamide 
• 1448295-71-3 (S)-1-benzyl-2-(1-fluorovinyl)pyrrolidine 

Relevant academic research and scientific papers

Conformational analysis and mu-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent.

Peptide carbamates containing the sequence H-Pro-Trp-PheNH2 showed in CDCl3 restricted conformations stabilized by the presence of a gamma-turn. To test the reliability of the peptides as endomorphin conformational models, we measured the affinities for mu-receptors labelled with [3H]-DAMGO. In particular, Cbz-Pro-Trp-PheNH2 displayed a nanomolar affinity.

Selective N-benzylation of amino acids under homogeneously catalyzed hydrogenation conditions

The chemoselective N-benzylation of the α-amino acids L-proline, L-serine and L-threonine is described using a reductive amination procedure with benzaldehyde catalyzed by homogeneous Rh-complexes affording N-benzyl protected amino acids.

Improved synthesis of proline-derived Ni(II) complexes of glycine: Versatile chiral equivalents of nucleophilic glycine for general asymmetric synthesis of α-amino acids

A synthetically practical and operationally convenient method for preparing (S)-2-[N-(N′-benzylprolyl)-amino]benzophenone (BPBP) and hitherto unknown (S)-2-[N-(N′-benzylprolyl)amino]-4-methylbenzophenone (4-Me-BPBP), (S)-2-[N-(N′-benzylprolyl)amino]-5-nitrobenzophenone (5-NO2-BPBP), and their corresponding Ni(II) complexes with glycine [GlyNi(II)BPBP], a widely used chiral equivalent of nucleophilic glycine, and new analogues [GlyNi(II)-4-Me-BPBP] and [GlyNi(II)-5-NO2-BPBP] is described. The key step of the method is the synthetically efficient amid bond formation between the corresponding o-aminobenzophenones, featuring significant steric shielding and low nucleophilicity of the amino functionality as well as sterically constrained (S)-N-benzylproline (BP).

l -Proline as a Valuable Scaffold for the Synthesis of Novel Enantiopure Neonicotinoids Analogs

In this research, six neonicotinoid analogs derived from l-proline were synthesized, characterized, and evaluated as insecticides against Xyleborus affinis. Most of the target compounds showed good to excellent insecticidal activity. To the best of our knowledge, this is the first report dealing with the use of enantiopure l-proline to get neonicotinoids. These results highlighted the compound 9 as an excellent candidate used as the lead chiral insecticide for future development. Additionally, molecular docking with the receptor and compound 9 was carried out to gain insight into its high activity when compared to dinotefuran. Finally, the neurotoxic evaluation of compound 9 showed lower toxicity than the classic neonicotinoid dinotefuran.

Preparation of labeled aromatic amino acids: Via late-stage18F-fluorination of chiral nickel and copper complexes

A general protocol for the preparation of 18F-labeled AAAs and α-methyl-AAAs applying alcohol-enhanced Cu-mediated radiofluorination of Bpin-substituted chiral complexes using Ni/Cu-BPX templates as double protecting groups is reported. The chiral auxiliaries are easily accessible from commercially available starting materials in a few synthetic steps. The versatility of the method was demonstrated by the high-yielding preparation of a series of [18F]F-AAAs and the successful implementation of the protocol into automated radiosynthesis modules. This journal is

Catalytic Transfer Hydrodebenzylation with Low Palladium Loading

A highly-efficient catalytic system for hydrodebenzylation reaction is described. The cleavage of O-benzyl and N-benzyl protecting groups was performed using an uncommonly low palladium loading (0.02–0.3 mol%; TON up to 5000) in a relatively short reaction time. The approach was used for a variety of substrates including pharmaceutically important precursors, and gram-scale deprotection reaction was shown. Transfer conditions together with easy-to-make Pd/C catalyst are the key features of this debenzylation scheme. (Figure presented.).

Synthesis of Chiral Spin-Labeled Amino Acids

Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.

Rational Design and Synthesis of Modified Teixobactin Analogues: In Vitro Antibacterial Activity against Staphylococcus aureus, Propionibacterium acnes and Pseudomonas aeruginosa

Teixobactin, a recently discovered depsipeptide that binds to bacterial lipid II and lipid III, provides a promising molecular scaffold for the design of new antimicrobials. Herein, we describe the synthesis and antimicrobial evaluation of systematically modified teixobactin analogues. The replacement of the Ile11 residue with aliphatic isosteres, the modification of the guanidino group at residue 10 and the introduction of a rigidifying residue, that is, dehydroamino acid, into the macrocyclic ring generated useful structure–activity information. Extensive antimicrobial susceptibility assessment against a panel of clinically relevant Staphylococcus aureus and Propionibacterium acnes strains led to the identification of the new lead compound, [Arg(Me)10,Nle11]teixobactin, with an excellent bactericidal activity (minimum inhibitory concentration (MIC)=2–4 μg mL?1). Significantly, the antimicrobial activity of several of the teixobactin analogues against the pathogenic Gram-negative Pseudomonas aeruginosa was “restored” when combined with the sub-MIC concentration of the outer membrane-disruptive antibiotic colistin. The antimicrobial effectiveness of a [Tfn10,Nle11]teixobactin (32 μg mL?1)–colistin (2 μg mL?1; 0.5×MIC) combination against P. aeruginosa PAO1 reveals, for the first time, an alternative therapeutic option in the treatment of Gram-negative infections.

N-ALKYLATED AMINO ACIDS AND OLIGOPEPTIDES, USES THEREOF AND METHODS FOR PROVIDING THEM.

The invention relates to the synthesis of amphiphilic amino acid derivatives, in particular to a method for the N-alkylation of an unprotected amino acid or the N-terminus of an oligopeptide substrate, comprising reacting said unprotected amino acid or oligopeptide substrate with an alcohol, e.g. a fatty alcohol, in the presence of a homogeneous transition metal catalyst.

Targeting Alzheimer's disease by investigating previously unexplored chemical space surrounding the cholinesterase inhibitor donepezil

A series of twenty seven acetylcholinesterase inhibitors, as potential agents for the treatment of Alzheimer's disease, were designed and synthesised based upon previously unexplored chemical space surrounding the molecular skeleton of the drug donepezil, which is currently used for the management of mild to severe Alzheimer's disease. Two series of analogues were prepared, the first looking at the replacement of the piperidine ring in donepezil with different sized saturated N-containing ring systems and the second looking at the introduction of different linkers between the indanone and piperidine rings in donepezil. The most active analogue 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (67) afforded an in vitro IC50value of 0.03 ± 0.07 μM against acetylcholinesterase with no cytotoxicity observed (IC50of >100 μM, SH-SY5Y cell line). In comparison donepezil had an IC50of 0.05 ± 0.06 μM and an observed cytotoxicity IC50of 15.54 ± 1.12 μM. Molecular modelling showed a strong correlation between activity and in silico binding in the active site of acetylcholinesterase.