55878-81-4Relevant academic research and scientific papers
Photochemical Chemoselective Alkylation of Tryptophan-Containing Peptides
Laroche, Benjamin,Tang, Xinjun,Archer, Gaétan,Di Sanza, Riccardo,Melchiorre, Paolo
supporting information, p. 285 - 289 (2021/01/26)
We report a photochemical method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor-acceptor complex generated between the tryptophan unit and pyridinium sal
Late-stage construction of stapled peptides through Fujiwara-Moritani reaction between tryptophan and olefins
Liu, Jiang,Lu, Qi,Wang, Peng,Zeng, Wei,Zhu, Qing
supporting information, p. 11661 - 11664 (2021/11/12)
Herein, the first example of a palladium-catalyzed Fujiwara-Moritani reaction for olefination of tryptophan (Trp) residues, free from directing groups, was presented. The developed reaction proceeds efficiently for peptide modification, ligation and pepti
Preparation method of trifluoromethylated polypeptide compound
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Paragraph 0085; 0087, (2020/12/30)
The invention discloses a preparation method of a trifluoromethylated polypeptide compound shown as a formula (II). The method comprises the following steps: by using a mixed solvent of DMF and waterin a volume ratio of 1:(1-4) as a reaction medium, reacting a polypeptide compound shown as a formula (I) with 1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one in the presence of a photocatalyst at roomtemperature under blue light for 3-8 hours, and after the reaction is completed, carrying out post-treatment on the obtained reaction mixture to obtain the trifluoromethylated polypeptide compound asshown in the formula (II). According to the method, the reaction is driven to be carried out under the irradiation of visible light, the reaction solvent is a mixed solvent of DMF and water, the greenchemical concept is better met, the product can be prepared in one step, the operation process is simple, raw material sources are commercialized and easy to obtain, the photocatalyst is utilized, good catalytic performance is achieved, the reaction condition is mild, and the site selectivity is high.
Copper-Promoted N-Arylation of the Indole Side Chain of Tryptophan Using Triarylbismuthines
Le Roch, Adrien,Chan, Hwai-Chien,Gagnon, Alexandre
supporting information, p. 5815 - 5819 (2020/07/25)
A simple protocol for the regioselective N-arylation of the indole side chain of tryptophan using triarylbismuth reagents as the arylating agent is reported. The reaction is catalyzed by copper(II) acetate, and operates in the presence of triethylamine or
Copper-Promoted O-Arylation of the Phenol Side Chain of Tyrosine Using Triarylbismuthines
Gagnon, Alexandre,Hébert, Martin,Le Roch, Adrien
supporting information, p. 5363 - 5367 (2020/08/27)
A general method for the O-arylation of the side chain of tyrosine using triarylbismuth reagents is reported. The reaction is mediated by copper diacetate, operates at 50 °C under oxygen in dichloromethane in the presence of pyridine, shows excellent functional group compatibility, and retains the integrity of the stereogenic center. The protocol was used to arylate the tyrosine residue of dipeptides and tripeptides.
Copper(ii) mediated facile and ultra fast peptide synthesis in methanol
Mali, Sachitanand M.,Jadhav, Sandip V.,Gopi, Hosahudya N.
, p. 7085 - 7087 (2012/08/14)
A novel, ultrafast, mild and scalable amide bond formation strategy in methanol using simple thioacids and amines is described. The mechanism suggests that the coupling reactions are initially mediated by CuSO4· 5H2O and subsequently catalyzed by in situ generated copper sulfide. The pure peptides were isolated in satisfactory yields in less than 5 minutes. The Royal Society of Chemistry 2012.
Selective inhibitors of the serine protease plasmin: Probing the S3 and S3′ subsites using a combinatorial library
Xue, Fengtian,Seto, Christopher T.
, p. 6908 - 6917 (2007/10/03)
A combinatorial library of 400 serine protease inhibitors with the general structure Cbz-Xaa-Trp-cyclohexanone-Trp-Yaa-OH has been constructed. The library was synthesized on the solid phase using mix-and-split synthesis, where 20 di
Polymer-supported mukaiyama reagent: A useful coupling reagent for the synthesis of esters and amides
Crosignani, Stefano,Gonzalez, Jerome,Swinnen, Dominique
, p. 4579 - 4582 (2007/10/03)
(Chemical equation presented) Polymer-supported N-alkyl-2-chloro pyridinium triflate was synthesized in one step from Wang resin. This reagent proved to be a very effective coupling reagent for the synthesis of esters or amides from carboxylic acids and alcohols or amines (primary and secondary).
Synthesis and evaluation of anti-inflammatory activity of 2-(4- isobutylphenyl)propionyl derivatives of amino acids and peptides
Belagali,Himaja
, p. 505 - 507 (2007/10/03)
A series of new 2-(4-isobutylphenyl)propionyl amino acids and peptide methyl esters have been synthesized by coupling ibuprofen with amino acid methyl esters and di- and tetra-peptide methyl esters. The structures of these compounds have been confirmed by elemental and spectral analyses. The anti-inflammatory activity of these compounds is also studied.
