38196-09-7Relevant academic research and scientific papers
Mild bioconjugation through the oxidative coupling of ortho-aminophenols and anilines with ferricyanide
Obermeyer, Allie C.,Jarman, John B.,Netirojjanakul, Chawita,El Muslemany, Kareem,Francis, Matthew B.
, p. 1057 - 1061 (2014)
Using a small-molecule-based screen, ferricyanide was identified as a mild and efficient oxidant for the coupling of anilines and o-aminophenols on protein substrates. This reaction is compatible with thiols and 1,2-diols, allowing its use in the creation
Easy oxidation and nitration of human myoglobin by nitrite and hydrogen peroxide
Nicolis, Stefania,Pennati, Andrea,Perani, Eleonora,Monzani, Enrico,Sanangelantoni, Anna Maria,Casella, Luigi
, p. 749 - 757 (2006)
The modification of human myoglobin (HMb) by reaction with nitrite and hydrogen peroxide has been investigated. This reaction is important because NO2- and H2O2 are formed in vivo under conditions of oxidative and nitrative stress, where protein derivatization has been often observed. The abundance of HMb in tissues and in the heart makes it a potential source and target of reactive species generated in the body. The oxidant and nitrating species produced by HMb/H 2O2/NO2- are nitrogen dioxide and peroxynitrite, which can react with exogenous substrates and endogenous protein resi dues. Tandem mass analysis of HMb modified by stoichiometric amounts of H2O2 and NO2- indicated the presence of two endogenous derivatizations: oxidation of C110 to sulfinic acid (76 %) and nitration of Y103 to 3-nitrotyrosine (44%). When higher concentrations of NO2- and H2O2 were used, nitration of Y146 and of the heme were also observed. The two-dimensional gel-electrophoretic analysis of the modified HMbs showed spots more acidic than that of wild-type HMb, a result in agreement with the formation of sulfinic acid and nitrotyrosine residues. By contrast, the reaction showed no evidence for the formation of protein homodimers, as observed in the reaction of HMb with H2O2 alone. Both HMb and the modified HMb are active in the H2O2/NO 2--dependent nitration of exogenous phenols. Their catalytic activity is quite similar and the endogenous modifications of HMb therefore have little effect on the reactivity of the protein intermediates.
Design, synthesis and antimicrobial evaluation of novel benzoxazole derivatives
Zhang, Wei,Liu, Jingbao,Macho, Jocelyn M.,Jiang, Xizhen,Xie, Dongsheng,Jiang, Faqin,Liu, Wenlu,Fu, Lei
, p. 7 - 14 (2017)
The synthesis of (S)-2-(4-tert-butylphenoxy)-3-(benzoxazol-5-yl) propanoic acid derivatives (2a-k) were described and their in?vitro antibacterial activities were determined against Gram-negative and -positive bacteria. These compounds were found to exert
Photoactivated bioconjugation between ortho -azidophenols and anilines: A facile approach to biomolecular photopatterning
El Muslemany, Kareem M.,Twite, Amy A.,Elsohly, Adel M.,Obermeyer, Allie C.,Mathies, Richard A.,Francis, Matthew B.
, p. 12600 - 12606 (2014)
Methods for the surface patterning of small molecules and biomolecules can yield useful platforms for drug screening, synthetic biology applications, diagnostics, and the immobilization of live cells. However, new techniques are needed to achieve the ease
N-terminal modification of proteins with o -aminophenols
Obermeyer, Allie C.,Jarman, John B.,Francis, Matthew B.
, p. 9572 - 9579 (2014)
The synthetic modification of proteins plays an important role in chemical biology and biomaterials science. These fields provide a constant need for chemical tools that can introduce new functionality in specific locations on protein surfaces. In this wo
Design, synthesis and antimicrobial activity of chiral 2-(substituted- hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives
Zhang, Wei,Liu, Wenlu,Jiang, Xizhen,Jiang, Faqin,Zhuang, Hao,Fu, Lei
experimental part, p. 3639 - 3650 (2011/11/05)
Chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives were synthesized and their antibacterial activities were evaluated against fungus, Gram-negative and Gram-positive bacteria. In general, these compounds showed in vitro acti
Reactions of p-Coumaric acid with nitrite: Product isolation and mechanism studies
Torres y Torres, Janelle L.,Rosazza, John P. N.
, p. 1486 - 1492 (2007/10/03)
p-Coumaric acid (1) is an abundant plant phenolic acid, a dietary chemoprotectant, and an antioxidant. The chemoprotective properties of I were demonstrated in vitro by its reaction with NaNO2 in H2O over a range of pH values. The reaction pathway of I with nitrite is dependent on pH. 4-Hydroxybenzaldehyde (3, 16%), 1′,4-dihydroxybenzeneacetaldehyde oxime (5, 59%), and 4-hydroxy-1′-oxo-benzeneacetaldehyde aldoxime (7, 26%) and 7-hydroxy-1,2(4H)-benzoxazin-4-one (11, 6%) were each formed at pH 2, whereas 4-(2-oxido-1,2,5-oxadiazol-3-yl)phenol (13) was formed at pH 3 (6%) and pH 7 and 10 (both 1%). Products were isolated and characterized by NMR and MS spectral analyses. Formation of benzoxazinone (11) requires the 4-phenolic functional group and the conjugated propenoic acid side chain of p-coumaric acid. The mechanism for nitrosation at pH 2 was examined by reacting I in H218O/NaNO2.
