64918-37-2Relevant articles and documents
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.
Synthesis of temperature-dependent elastin-like peptide-modified dendrimer for drug delivery
Kojima, Chie,Irie, Kotaro
, p. 714 - 721 (2014/01/17)
Dendrimers are synthetic macromolecules with a unique structure that are potential unimolecular drug carriers and potential scaffolds for peptides. Elastin is one of the main components of the extracellular matrix, as well as a temperature-sensitive biomacromolecule. Val-Pro-Gly-Val-Gly repeats, an elastin-like peptide, have been used for designing artificial elastin molecules. In this study, we have synthesized a novel type of temperature-dependent drug carrier by conjugating Ac-Val-Pro-Gly-Val-Gly to a dendrimer, named elastin-mimetic dendrimer. The elastin-mimetic dendrimer formed β-turn structure by heating. The elastin-mimetic dendrimer exhibited the inverse phase transition, depending on pH and NaCl concentration in addition to temperature. The elastin-mimetic dendrimer could encapsulate a model drug, rose bengal, even though the complex stability was similar to the dendrimer without elastin-like peptide. Therefore, the elastin-mimetic dendrimer is a potential drug carrier with temperature- and pH-dependent properties. (134 words)
Design and synthesis of tryptophan containing peptides as potential analgesic and anti-inflammatory agents
Suhas,Gowda, D.Channe
scheme or table, p. 535 - 540 (2012/09/22)
A new series of smaller peptides with tryptophan at C-terminal and varying N-protected amino acids/peptides were designed, synthesized and characterized by analytical and spectroscopic techniques. Analgesic and anti-inflammatory properties of these peptides were carried out in vivo using tail-flick method and carrageenan-induced paw edema method, respectively, at different doses and different time intervals. Most of the peptides synthesized displayed enhanced activity, and particularly tetra and hexapeptides 29-31 were found to be even more potent than the reference standards used. Moreover, some peptides have exhibited promising activity even after 24h of administration, whereas the reference standards were active only up to 3h. Further, the compounds did not present any ulcerogenic liability.
