74221-51-5Relevant academic research and scientific papers
Macrocyclization of biaryl-bridged peptides through late-stage palladium-catalyzed C(sp2)-H Arylation
Bai, Qingqing,Bai, Zengbing,Wang, Huan
, p. 8225 - 8228 (2019)
Macrocyclic peptides are promising scaffolds of bioactive compounds and clinical therapeutics. Herein, we develop a strategy for the macrocyclization of biaryl-bridged peptides through late-stage Pd-catalyzed C(sp2)-H arylation. This method dis
Structure-CaSR-activity relation of kokumi γ-glutamyl peptides
Amino, Yusuke,Nakazawa, Masakazu,Kaneko, Megumi,Miyaki, Takashi,Miyamura, Naohiro,Maruyama, Yutaka,Eto, Yuzuru
, p. 1181 - 1189 (2016/08/11)
Modulation of the calcium sensing receptor (CaSR) is one of the physiological activities of γ-glutamyl peptides such as glutathione (γ-glutamylcysteinylglycine). γ-Glutamyl peptides also possess a flavoring effect, i.e., sensory activity of kokumi substances, which modifies the five basic tastes when added to food. These activities have been shown to be positively correlated, suggesting that kokumi γ-glutamyl peptides are perceived through CaSRs in humans. Our research is based on the hypothesis that the discovery of highly active CaSR agonist peptides will lead to the creation of practical kokumi peptides. Through continuous study of the structure-CaSR-activity relation of a large number of γ-glutamyl peptides, we have determined that the structural requirements for intense CaSR activity of γ-glutamyl peptides are as follows: existence of an N-terminal γ-L-glutamyl residue; existence of a moderately sized, aliphatic, neutral substituent at the second residue in an L-configuration; and existence of a C-terminal carboxylic acid, preferably with the existence of glycine as the third constituent. By the sensory analysis of γ-glutamyl peptides selected by screening using the CaSR activity assay, γ-glutamylvalylglycine was found to be a potent kokumi peptide. Furthermore, norvaline-containing γ-glutamyl peptides, i.e., γ-glutamylnorvalylglycine and γ-glutamylnorvaline, possessed excellent sensory activity of kokumi substances. A novel, practical industrial synthesis of regiospecific γ-glutamyl peptides is also required for their commercialization, which was achieved through the ring opening reaction of N-α-carbobenzoxy-L-glutamic anhydride and amino acids or peptides in the presence of N-hydroxysuccinimide.
Kokumi-imparting agent
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, (2016/08/17)
The present invention encompasses a method for screening for a kokumi-imparting substance by using the calcium receptor activity as an index, a composition containing a kokumi-imparting substance obtained by the screening method, a method for producing fo
CALCIUM RECEPTOR ACTIVATOR
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Page/Page column 19-21, (2008/06/13)
A calcium receptor activator containing one or more kinds of substances selected from á-Glu-Cys-Gly, á-Glu-Cys(SNO)-Gly, á-Glu-Ala, á-Glu-Gly, á-Glu-Cys, á-Glu-Met, á-Glu-Thr, á-Glu-Val, á-Glu-Orn, Asp-Gly, Cys-Gly, Cys-Met, Glu-Cys, Gly-Cys, Leu-Asp, D-Cys, á-Glu-Met(O), á-Glu-Val-Val, á-Glu-Val-Glu, á-Glu-Val-Lys, á-Glu- á-Glu-Val, á-Glu-Val-NH2, á-Glu-Val-ol, á-Glu-Ser, á-Glu-Tau, á-Glu-Cys(S-Me)(O), á-Glu-Leu, á-Glu-Ile, á-Glu-t-Leu, á-Glu-Cys(S-allyl)-Gly, á-Glu-Gly-Gly, á-Glu-Val-Phe, á-Glu-Val-Ser, á-Glu-Val-Pro, á-Glu-Val-Arg, á-Glu-Val-Asp, á-Glu-Val-Met, á-Glu-Val-Thr, á-Glu-Val-His, á-Glu-Val-Asn,á-Glu-Val-Gln, á-Glu-Val-Cys, á-Glu-Val-Orn, á-Glu-Ser-Gly, á-Glu-Cys(S-Me), á-Glu-Abu-Gly, á-Glu-Cys(S-Me)-Gly, and á-Glu-Val-Gly.
Kinetic studies on oxidation of Gly-Val-Gly, Gly-Phe-Ply and Ala-Val-Gly using Mn(III)
Gowda, B.K. Kempe,Rangappa,Gowda, D. Channe
, p. 1039 - 1044 (2007/10/03)
The fragments of elastin sequences, glycyl-valyl-glycine (GVG), glycyl-phenylalanyl-glycine (GFG) and alanyl-valyl-glycine (AVG) have been synthesized by classical solution phase method and characterized. Kinetics of oxidation of these tripeptides (TP) by Mn(III) has been studied in the presence of sulphate ions in acidic medium at 25°C. The reaction follows spectrophotometrically at Λmax 500 nm. A first order dependence of rate on both [Mn(III)] and [TP] has been observed. The rate is independent of concentrations of reduction product, Mn(II) and hydrogen ions. Effects of varying dielectric constant of the medium and addition of anions such as sulphate, chloride and perchlorate have been studied. Activation parameters have been evaluated using Arrhenius and Erying plots. The oxidation products are isolated and characterized. A tentative mechanism involving the reaction of TP with Mn(III) in the rate-limiting step is suggested. The effect of hydrophobicity of amino acids on the rate of oxidation is discussed.
Amino acids and peptides. LIV. Application of 2-adamantyl derivatives as protecting groups to the synthesis of peptide fragments related to Sulfolobus solifataricus ribonuclease. I
Okada, Yoshio,Joshi, Shima,Shintomi, Noriyuki,Kondo, Yukihiro,Tsuda, Yuko,Ohgi, Kazuko,Irie, Masachika
, p. 1089 - 1096 (2007/10/03)
The 2-adamantyloxycarbonyl group was employed for the protection of the ε-amino group of Lys and the hydroxyl group of Tyr, and the 2-adamantyl ester was employed for the protection of the β-carboxyl group of Asp in order to construct eight peptide segments as building blocks for the preparation of peptide fragments related to the sequence of Sulfolobus solifataricus Ribonuclease. The usefulness of the above protecting groups developed in our laboratory was confirmed.
Emerimicins III and IV and their ethylalanine12 epimers. Facilitated chemical-enzymatic synthesis and a qualitative evaluation of their solution structures
Slomczynska, Urszula,Beusen, Denise D.,Zabrocki, Janusz,Kociolek, Karol,Redlinski, Adam,Rensser, Fritz,Hutton, William C.,Leplawy, Miroslaw T.,Marshall, Garland R.
, p. 4095 - 4106 (2007/10/02)
The peptaibol antibiotics, emerimicin III and IV (Ac-Phe1-MeA2-MeA3-MeA4-VaI 5-Gly6-Leu7-MeA8-MeA 9-Hyp10-Gln11-R-EtA12-Hyp
