1117-77-7Relevant academic research and scientific papers
Hydrogen bonding of 1-cyclohexyluracil with acetylglycine N-methylamide
Carmona, P.,Garcia-Ramos, J. V.
, p. 155 - 158 (1984)
I.r. spectroscopy was used to determine the enthalpy of hydrogen bond complex formation of 1-cyclohexyluracil with acetylglycine N-methylamide, in chloroform solution.Enthalpy of association is found to be -5.4 Kcal/mole for the dimer of acetylglycine N-methylamide and -4.7 Kcal/mole for the mixed dimers of this dipeptide with 1-cyclohexyluracil.These thermodynamic parameters and the i.r. spectra of the solutions suggest that the structures of these dimers are cyclic.
Novel carboxylated pyrroline-2-one derivatives bearing a phenylhydrazine moiety: Design, synthesis, antifungal evaluation and 3D-QSAR analysis
Chen, Min,Zhang, Lizhi,Lu, Aimin,Wang, Xiaobin,Si, Weijie,Yan, Jinghua,Yang, Chunlong
, (2020)
Aiming to discover novel high-efficient antifungal leads that possess an innovative action mechanism, twenty-three carboxylated pyrroline-2-one derivatives, bearing a phenylhydrazine moiety, were rationally designed and firstly prepared in this letter. The in vitro bioassays showed that most of the compounds possessed excellent antifungal effects with the EC50 values of less than 1 μg/mL against the phytopathogenic fungi Fusarium graminearum (Fg), Botrytis cinerea (Bc), Rhizoctonia solani (Rs) and Colletotrichum capsici (Cc). The further bioassays showed that the compound 6u showed the comparable in vivo control effect with carbendazim against fusarium head blight and rice sheath blight. The 3D-QSAR model revealed the pivotal effects of a bulky electron-donating group at the 1-position of pyrrole ring, a bulky electron-withdrawing group at the 4-position of phenyl ring and a small alkyl at the carbonate group on the anti-Rs activities of target compounds. The abnormal mycelial morphology and delayed spore germination were observed in the treatments of compound 6u. Given the excellent and broad-spectrum antifungal effects the target compounds have, we unfeignedly anticipated that the above finding could motivate the discovery of high-efficient antifungal leads, which might possess an innovative action mechanism against phytopathogenic fungi.
Oxidative Damage in Aliphatic Amino Acids and Di- and Tripeptides by the Environmental Free Radical Oxidant NO3?: the Role of the Amide Bond Revealed by Kinetic and Computational Studies
Nathanael, Joses G.,Wille, Uta
, p. 3405 - 3418 (2019)
Kinetic and computational data reveal a complex behavior of the important environmental free radical oxidant NO3? in its reactions with aliphatic amino acids and di- and tripeptides, suggesting that attack at the amide N-H bond in the peptide backbone is a highly viable pathway, which proceeds through a proton-coupled electron transfer (PCET) mechanism with a rate coefficient of about 1 × 106 M-1 s-1 in acetonitrile. Similar rate coefficients were determined for hydrogen abstraction from the α-carbon and from tertiary C-H bonds in the side chain. The obtained rate coefficients for the reaction of NO3? with aliphatic di- and tripeptides suggest that attack occurs at all of these sites in each individual amino acid residue, which makes aliphatic peptide sequences highly vulnerable to NO3?-induced oxidative damage. No evidence for amide neighboring group effects, which have previously been found to facilitate radical-induced side-chain damage in phenylalanine, was found for the reaction of NO3? with side chains in aliphatic peptides.
Ligand-dependent site selectivity in the Rh(II)-catalyzed decomposition of a glycine-derived diazo acetoacetamide
Prein, Michael,Padwa, Albert
, p. 6981 - 6984 (1996)
The product distribution obtained from the Rh(II)-catalyzed decomposition of α-diazoimide 1 can be selectively controlled by the proper choice of catalyst. While perfluorinated ligands favor isomunchnone formation, products derived from 6-ring cyclization are preferred using Rh2(OAc)4. The effect can be modulated by the addition Sc(OTf)3 as a Lewis acid.
Conformational Analysis of Linear Peptides. 3. Temperature Dependence of NH Chemical Shifts in Chloroform
Stevens, E. S.,Sugawara, N.,Bonora, G. M.,Toniolo, C.
, p. 7048 - 7050 (1980)
The following conclusions concerning NH chemical shifts for peptides in chloroform are based on numerous observations on small model peptides reported here and also on data in the literature. (1) The temperature dependence of chemical chift for an amide NH proton exposed to solvent in chloroform solutions is 0.0024 +/- 0.0005 ppm K-1. (2) Small temperature dependencies can also be observed if the NH group is shielded from solvent and remains shielded over the temperature range of the 1H NMR measurements. (3) Larger temperature dependencies are observed if the NH group is shielded from solvent initially but becomes exposed with increasing temperature, a situation which holds when intermolecular self-association is significant or when intermolecularly hydrogen-bonded conformations unfold as the temperature is increased.Previously proposed conformations based on the presumption that NH chemical shifts display in chloroform solution the same behavior as in strongly polar solvents are herein reexamined.
Proline-rich proteins - Deriving a basis for residue-based selectivity in polyphenolic binding
Croft,Foley
, p. 1594 - 1600 (2008)
1H NMR titration experiments have been used to establish that minimal proline-based models show enhanced binding selectivity towards phenol in CDCl3, relative to other similarly protected amino acid residues. Cooperative binding effects appear to play a role, with sarcosine models affording binding constants to phenol intermediate to those obtained from proline models and other amino acid models. The mechanism for binding, based on DFT calculations and the application of Hunter's molecular recognition toolbox model, cannot be solely attributed to hydrogen bond strength, and appears to be mediated through C-H-π bonds and the rotational freedom of the amide substrate. The Royal Society of Chemistry 2008.
Methyl 2-(Bromomethyl)acrylate, Methyl Acrylate, and Glycine in the Synthesis of Functionalized Pyrrolidones
Selezneva,Valiullina,Galeeva,Spirikhin,Miftakhov
, p. 1665 - 1669 (2018)
Possible application of methyl 2-(bromomethyl)acrylate, methyl acrylate, and glycine in the synthesis of functionalized pyrrolidones was considered.
A new type of amide formation from thiocarboxylic acid and alkyl azide
Park, Sang-Don,Oh, Jung-Hee,Lim, Dongyeol
, p. 6309 - 6311 (2002)
We studied the coupling of thiocarboxylic acid and alkyl azide using various triaryl phosphines. Amide formation greater than 95% was achieved when the free-formation of Staudinger intermediate with electron deficient triaryl phosphines was employed.
1,1'-OXALYLDIIMIDAZOLE, A NEW REAGENT FOR ACTIVATION OF CARBOXYLIC ACID
Murata, Shizuaki
, p. 1819 - 1820 (1983)
Carboxylic acids and their salts are converted into the 1-acylimidazoles by the title reagent.This reaction is applied for esterification of fatty acids.
A new method for peptide synthesis in the N→C direction: Amide assembly through silver-promoted reaction of thioamides
Pourvali, Aysa,Cochrane, James R.,Hutton, Craig A.
supporting information, p. 15963 - 15966 (2015/01/09)
The Ag(i)-promoted coupling of amino acids and peptides with amino ester thioamides generates peptide imides without epimerisation. The peptide imides undergo regioselective hydrolysis under mild conditions to generate native peptides. This method was employed to prepare the pentapeptide thymopentin in the N→C direction, in high yield and purity.
