38155-19-0Relevant articles and documents
An effective and safe enkephalin analog for antinociception
Durgarao Viswanadham,B?ttger, Roland,Hohenwarter, Lukas,Nguyen, Anne,Rouhollahi, Elham,Smith, Alexander,Tsai, Yi-Hsuan,Chang, Yuan-Yu,Ortiz, Christopher Llynard,Yang, Lee-Wei,Jimenez, Liliana,Li, Siyuan,Hur, Chan,Li, Shyh-Dar
, (2021/07/10)
Opioids account for 69,000 overdose deaths per annum worldwide and cause serious side effects. Safer analgesics are urgently needed. The endogenous opioid peptide Leu-Enkephalin (Leu-ENK) is ineffective when introduced peripherally due to poor stability a
Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones
Shugrue, Christopher R.,Featherston, Aaron L.,Lackner, Rachel M.,Lin, Angela,Miller, Scott J.
supporting information, p. 4491 - 4504 (2018/04/26)
Phosphothreonine (pThr)-embedded peptide catalysts are found to mediate the reductive amination of 3-amidocyclohexanones with divergent selectivity. The choice of peptide sequence can be used to alter the diastereoselectivity to favor either the cis-product or trans-product, which are obtained in up to 93:7 er. NMR studies and DFT calculations are reported and indicate that both pathways rely on secondary interactions between substrate and catalyst to achieve selectivity. Furthermore, catalysts appear to accomplish a parallel kinetic resolution of the substrates. The facility for phosphopeptides to tune reactivity and access multiple products in reductive aminations may translate to the diversification of complex substrates, such as natural products, at numerous reactive sites.
Synthesis, characterization and antimicrobial activity of protected dipeptides and their deprotected analogs
Gill, Jatinder Pal Kaur,Singh, Simranjeet,Sethi, Nidhi
, p. 417 - 421 (2015/06/30)
Peptides are the chemical compounds which consist of amino acids coupled together by peptide linkage. Peptide derivatives are synthesized by coupling the carboxyl group of one amino acid with amino group of other. Due to the possibilities of fortuitous and unintentional reactions, various protecting groups are used to protect the carboxylic acid as well as amino groups of both the amino acids. These peptide derivatives are associated with a variety of pharmacological activities including antibacterial and antifungal activities. While doing our analysis some of the dipeptides were synthesized in a reasonable yield and purity which were fully characterised by FTIR and H1 NMR. The antimicrobial activity of these derivatives was studied and these were found to be active against two strains of fungi (Aspergillus fumigatus & Pencillium chrysogenum) and two strains of bacteria (E. coli and Salmonella typhimurium). This provides for a future insight to work on the synthesis of these dipeptide derivatives to achieve their stability.
Synthesis of novel sugar amino acids by Curtius rearrangement
Van Well, Renate M.,Overkleeft, Herman S.,Van Boom, Jacques H.,Coop, Andrew,Wang, Jia Bei,Wang, Hongyan,Van der Marel, Gijsbert A.,Overhand, Mark
, p. 1704 - 1710 (2007/10/03)
Sugar amino acids (SAAs) bearing an amine group on the anomeric position are a challenging class of SAAs to synthesize due to the inherent instability of glycosylamines. We developed a novel synthetic strategy towards both furanoid and pyranoid δ-SAAs of
Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: Synthesis and mechanism of action
Martyn, Derek C.,Vernall, Andrea J.,Clark, Bruce M.,Abell, Andrew D.
, p. 2103 - 2110 (2007/10/03)
13C NMR and mass spectrometry studies have been used to demonstrate that the inhibition of α-chymotrypsin by N-sulfonylhydroxymethylpyrrole inhibitors (10) is non-covalent. Hydroxyalkylpyrroles in which an electron-withdrawing group (acyl substituent) is introduced at the alternative C2 position have been synthesised and also shown to inactivate α-chymotrypsin. SAR studies on this class suggests that the incorporation of phenylalanine at C2 is favoured, however, there is little gain in introducing a hydrophobic substituent at C5.
Met-Ile-Phe-Leu derivatives: Full and partial agonists of human neutrophil formylpeptide receptors
Dalpiaz, Alessandro,Scatturin, Angelo,Vertuani, Gianni,Pecoraro, Rita,Borea, Pier Andrea,Varani, Katia,Traniello, Serena,Spisani, Susanna
, p. 327 - 333 (2007/10/03)
The biological action of a series of Met-Ile-Phe-Leu analogues was analyzed on human neutrophils, to evaluate their ability to interact with formylpeptide receptors and to induce the related neutrophil responses. Three in vitro assays were carried out: receptor binding, chemotaxis and superoxide anion release. Our results demonstrate that formyl-Met-Ile-Phe-Leu derivatives act as more potent full agonists than formyl-Met-Leu-Phe, the tripeptide normally used as a model chemoattractant for the study of cell functions. On the other hand, the presence of N-ureidoisopropyl substituent in tetrapeptides imparts weak partial agonist properties. It has furthermore been demonstrated that the C-terminal methyl esterification or amination weakly influences the properties of tetrapeptide homologues. Finally, t-Boc-Met-Ile-Phe-Leu derivatives do not appear able to interact with formylpeptide receptors.
Differences arising in human neutrophil activation passing from N-formyl to N-acetyl-oligopeptides
Spisani, Susanna,Cavicchioni, Giorgio
, p. 252 - 259 (2007/10/03)
N-formyl- and N-acetyl-peptides were synthesized and compared in order to understand which features can best elicit biological responses. The behavior of N-formyl-peptides confirms the previously found sequential obligations in the residues, while acetyl-
Synthesis of new glycopeptides; application to the preparation of N-(5-enkephalyl)-α-D-galacto-oct-6-enopyranuronamide
Coutrot, Philippe,Grison, Claude,Lecouvey, Marc
, p. 27 - 46 (2007/10/03)
The synthesis of new glycopeptides in which the peptidic moiety is linked to the glucidic part through a keto α,β-ethylenic handle is described.Two routes have been studied.The first strategy devised uses Horner reagents derived from N-substituted (diethy
The Redox-Sensitive, Colored N-3-(3',6'-Dioxo-2',4',5'-Trimethylcyclohexa-1',4'-Diene)-3,3-Dimethylpropionyl (Q) Amino-Protecting Group
Carpino, Louis A.,Nowshad, Fatemeh
, p. 7009 - 7012 (2007/10/02)
Amino acids bearing the title (Q) protecting group undergo coupling without racemization via the mixed anhydride technique.Selective deblocking via Na2S2O4.
Retro Aza Diels-Alder Reactions of 2-Azanorbornenes: Improved Methods for the Unmasking of Primary Amines
Grieco, Paul A.,Clark, Jerry D.
, p. 2271 - 2272 (2007/10/02)
The unmasking of primary amines via the heterocycloreversion of N-alkyl-2-azanorbornenes can be catalyzed by either copper(II) or a sulfonic acid based ion exchange resin which obviates the necessity of employing a reactive dienophile to trap the cyclopentadiene as it is produced.