52071-64-4

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 3392-10-7 tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 96792-04-0 (-)-(S)-tert-butyl-2-<(hydroxyamino)carbonyl>pyrrolidine-1-carboxylate 
• 133010-05-6 tert-butyl 2-(fluorocarbonyl)pyrrolidine-1-carboxylate 

Downstream Products

• 54793-80-5 (S)-proline-(S)-phenylalanine methyl ester 
• 13589-02-1 L-prolyl-L-phenylalanine 
• 564489-29-8 (S)-tert-butyl 2-(((S)-1-((S)-3-hydroxy-1-methoxy-1-oxopropane-2-yl-amino)-1-oxo-3-phenylpropane-2-yl)carbamoyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Conformational studies of new pseudotripeptide with pyrazine amidoxime motif and simplified analogs using IR, NMR spectroscopy, and molecular dynamic simulations

Solution structures of new pyrazine-based pseudotripeptide with amidoxime function and simplified pseudodipeptide analogs were determined by a combination of IR and NMR spectroscopic studies and molecular dynamic simulations using explicit chloroform as a

Pro-phe derivatives as organocatalysts in asymmetric aldol reaction

The aldol reaction which is the most important one among the C-C bond forming reactions, is widely used by synthetic organic chemists to obtain β-hydroxycarbonyl compounds which are important starting components for biologically active compounds in optica

Asymmetric Organocatalysis Accelerated via Self-Assembled Minimal Structures

Self-assembling minimalistic peptides embedded with an organocatalytic moiety were designed. By controlling the formation of fibrils via external intervention, it was shown that the activation is accelerated when the organocatalyst is in its supramolecula

Synthesis of new di- And triamides as potential organocatalysts for asymmetric aldol reaction in water

New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0 °C in the presence of benzoic acid as co-catalyst. (S)-me

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.

Total syntheses of (?)-emestrin H and (?)-asteroxepin

First total syntheses of (?)-emestrin H and (?)-asteroxepin are described. To find the appropriate protecting group on the amide nitrogen of the diketopiperazine core, we conducted model studies using a simple diketopiperazine derivative. As a result, allyloxymethyl (Allom) group was the most suitable protecting group, which tolerated Nicolaou's sulfenylation conditions, and was easily cleavable under the mild conditions using Pd(PPh3)4 and N,N-dimethylbarbituric acid leaving methylthioethers intact. The general utility of Allom group for protection of amides was studied using simple substrates. Finally, the effectiveness of Allom group was proved by the accomplishment of the first total synthesis of (?)-emestrin H. Allom group was robust enough during installation of two methylthioethers to the diketopiperazine core and easily removed at the final step. The first total synthesis of (?)-asteroxepin was also completed by acylation of (?)-emestrin H.

Synthesis of novel proline-based imidazolium ionic liquids

Abstract: A series of eight novel proline functionalized dipeptide imidazolium ionic liquids (DPILs), i.e. Boc-[Pro-Pro-EMIM], Boc-[Pro-Val-EMIM], Boc-[Pro-Ala-EMIM], Boc-[Pro-Phe-EMIM] containing [Cl] and [NTf2] anions were synthesized via a f

Engineered Substrate for Cyclooxygenase-2: A Pentapeptide Isoconformational to Arachidonic Acid for Managing Inflammation

Beyond the conventional mode of working of anti-inflammatory agents through enzyme inhibition, herein, COX-2 was provided with an alternate substrate. A proline-centered pentapeptide isoconformational to arachidonic acid, which exhibited appreciable selectivity for COX-2, overcoming acetic acid- and formalin-induced pain in rats to almost 80%, was treated as a substrate by the enzyme. Remarkably, COX-2 metabolized the pentapeptide into small fragments consisting mainly of di- and tripeptides that ensured the safe breakdown of the peptide under in vivo conditions. The kinetic parameter Kcat/Km for COX-2-mediated metabolism of the peptide (6.3 × 105 M-1 s-1) was quite similar to 9.5 × 105 M-1 s-1 for arachidonic acid. Evidenced by the molecular dynamic studies and the use of Y385F COX-2, it was observed that the breakage of the pentapeptide has probably been taken place through H-bond activation of the peptide bond by the side chains of Y385 and S530.

Synthesis of 3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione [cyclo(Pro-Phe)] was synthesized by cyclization of prolylphenylalanine and phenylalanylproline methyl esters which were prepared from the corresponding Boc-protected amino acids.

New and effective proline-based catalysts for asymmetric aldol reaction in water

New proline diamide organocatalysts with Pro-Phe peptide bonds were synthesized and their catalytic activities in asymmetric direct aldol reactions of aliphatic ketones with aromatic aldehydes were investigated. Catalyst 6a showed good enantioselectivity