22248-60-8Relevant academic research and scientific papers
Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp3)?H Alkylation of Glycine and Peptides
Wang, Chao,Guo, Mengzhun,Qi, Rupeng,Shang, Qinyu,Liu, Qiang,Wang, Shan,Zhao, Long,Wang, Rui,Xu, Zhaoqing
, p. 15841 - 15846 (2018/11/23)
Despite a well-developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible-light-induced Cu-catalyzed decarboxylative C(sp3)?H alkylation of glycine for preparing α-alkylated unnatural α-amino acids. It merits mentioning that the mild conditions and the good functional-group tolerance allow the modification of peptides using this method. The mechanistic studies revealed that a radical–radical coupling pathway is involved in the reaction.
Synthesis and electrochemical studies of disubstituted ferrocene/dipeptide conjugates with sulfur-containing side chains
Scully, Conor C.G.,Rutledge, Peter J.
scheme or table, p. 5653 - 5659 (2010/10/02)
A series of 1 1'-disubstituted ferrocenoyl peptides incorporating dipeptide sidearms has been synthesized and studied electrochemically. The target peptides include ferrocene as an electrochemical reporter, sulfur-containing amino acids (L-methionine, S-methyl-L-cysteine, S-trityl-L-cysteine, S-benzhydryl-L- cysteine) as metal binding agents, and amino acids with non-polar side chains (L-alanine, L-valine, L-phenylalanine) as spacers between reporter and metal binding groups. Ferrocene/dipeptide conjugates were prepared using solution phase peptide synthesis methods employing a BOC-protecting group strategy and HBTU- (O-(benzotriazol-1-yl)-N, N, N', N'-tetramethyluronium hexafluorophosphate) mediated peptide coupling. The electrochemical properties of these 1, 1'-substituted ferrocenoyl peptides have been characterized using cyclic voltammetry. All exhibit fully reversible one electron oxidation steps; forward sweep half wave peaks (EF), reverse sweep half wave peaks (ER), peak separations (DEP) and half wave potentials (E1/2) are reported. Finally, towards the goal of utilizing ferrocenoyl peptides to detect heavy metals in solution, the response of these ferrocene/dipeptide conjugates to metal cations (zinc(II), mercury(II), cadmium(II), lead(II), silver(I)) has been examined. Monitoring changes in the potential of the Fe(II)/Fe(III) redox couple to follow peptide/metal interactions, we have probed the influence of the spacer unit between the redox reporter and the metal-binding amino acid, and shown that these systems respond to mercury(II) more strongly than to other heavy metal ions.
Synthesis and biological evaluation of potential bisubstrate inhibitors of protein farnesyltransferase. Design and synthesis of functionalized imidazoles
De Figueiredo, Renata Marcia,Coudray, Laetitia,Dubois, Joelle
, p. 3299 - 3309 (2008/09/20)
A novel series of compounds, derived from 2,5-functionalized imidazoles, have been synthesized as potential bisubstrate inhibitors of protein farnesyltransferase (FTase) using structure-based design. These compounds have a 1,4-diacid chain and a tripeptid
Phosphorus-based Reagents in Peptide Synthesis: Synthesis of Methionine-Enkephalin and the Solution Conformation of its N-Diphenylphosphinoyl Derivative
Smith, D. David,Boyd, Kenneth G.,Hopton, David,Baxter, Robert L.,Ramage, Robert
, p. 551 - 556 (2007/10/02)
Met5enkephalin 1 was synthesized by solution phase synthesis using the diphenylphosphinoyl (Dpp) group for α-amino group protection and diphenylphosphinoyl-carboxylic acid mixed anhydrides for carboxylate activation.These reagents proved to be compatible with both tyrosine and methionine side chain functionalities.A (1)H NMR study of the solution conformation of the N-terminal-protected pentapeptide DppMe5enkephalin 2 in dimethyl sulfoxide suggests that the peptide backbone of this derivative adopts a major conformation possessing a type I' β-bend between residues Gly2-Gyl3 with the side chains of the Tyr1 and Phe4 lying on the same side of the plane of the bend.The predominant conformation of the Phe4 and Met5 side chains appear to be tg+.
Selectivity in the Trimethylsilylation and Acylation of Peptide Bonds, and its Application to Modification of the Enkephalins
Davies, John S.,Merritt, Raymond K.,Treadgold, Richard C.,Morley, John S.
, p. 2939 - 2948 (2007/10/02)
N.m.r. spectra of N-acylated peptides, formed by reaction of protected peptides with silylating agents followed by acylation, have provided a means for assessing selectivity in the acylation of amide bonds.Amino-acids such as valine and phenylalanine prev
Synthesis and pharmacological study of some enkephalin analogs in relation to the plurality of opiate receptors
Audigier,Mazarguil,Gout,Cros
, p. 173 - 177 (2007/10/02)
We have synthesized a series of enkephalin analogs and measured their affinity for each type of 'opiate' receptor, the μ receptor and the δ receptor. Furthermore, we have determined their respective antinociceptive activity after intracerebroventricular i
