619-73-8Relevant articles and documents
Cyclic voltammetry and XPS analyses of graphite felt derivatized by non-Kolbe reactions in aqueous media
Geneste, Florence,Cadoret, Mael,Moinet, Claude,Jezequel, Guy
, p. 1261 - 1266 (2002)
This present work describes a preliminary study of modification of graphite felt for future applications in indirect electrolysis. The anodic oxidation of electroactive carboxylate compounds was achieved in aqueous media. The derivatization of the electrode was highlighted by cyclic voltammetry and XPS analyses. Interestingly, the grafting process led to chemically stable covalent attachment of nitroaryl species on the graphite felt with simultaneous increase of its real surface area. The comparison with the process performed in acetonitrile underlines the role of graphite oxidation in the immobilization of the molecules on the felt.
Structural basis of the broad substrate tolerance of the antibody 7B9-catalyzed hydrolysis of p-nitrobenzyl esters
Miyamoto, Naoki,Yoshimura, Miho,Okubo, Yuji,Suzuki-Nagata, Kayo,Tsumuraya, Takeshi,Ito, Nobutoshi,Fujii, Ikuo
, p. 1412 - 1417 (2018)
Catalytic antibody 7B9, which was elicited against p-nitrobenzyl phosphonate transition-state analogue (TSA) 1, hydrolyzes a wide range of p-nitrobenzyl monoesters and thus shows broad substrate tolerance. To reveal the molecular basis of this substrate tolerance, the 7B9 Fab fragment complexed with p-nitrobenzyl ethylphosphonate 2 was crystallized and the three-dimensional structure was determined. The crystal structure showed that the strongly antigenic p-nitrobenzyl moiety occupied a relatively shallow antigen-combining site and therefore the alkyl moiety was located outside the pocket. These results support the observed broad substrate tolerance of 7B9 and help rationalize how 7B9 can catalyze various p-nitrobenzyl ester derivatives. The crystal structure also showed that three amino acid residues (AsnH33, SerH95, and ArgL96) were placed in key positions to form hydrogen bonds with the phosphonate oxygens of the transitions-state analogue. In addition, the role of these amino acid residues was examined by site-directed mutagenesis to alanine: all mutants (AsnH33Ala, SerH95Ala, and ArgL96Ala) showed no detectable catalytic activity. Coupling the findings from our structural studies with these mutagenesis results clarified the structural basis of the observed broad substrate tolerance of antibody 7B9-catalyzed hydrolyses. Our findings provide new strategies for the generation of catalytic antibodies that accept a broad range of substrates, aiding their practical application in synthetic organic chemistry.
Primary Amine–Promoted Ring Opening in Carbapenem-derived p-Nitrobenzyl Esters
Galeeva, А.М.,Lobov, А. N.,Miftakhov, М. S.,Valiullina, Z. R.
, (2020)
Abstract: Ethylamine and ethanolamine react with 4-nitrobenzyl (4R,5S,6S)-3-[(2-furylmethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, leading to the opening of the β-lactam ring by C7–N bond c
Synthesis of 10,10-dimethylprostaglandin F1 and F2 analogues
Plantema,De Koning,Huisman
, p. 268 - 275 (1983)
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Palladium(II)-Catalyzed C(sp2)-H Bond Activation/C-N Bond Cleavage Annulation of N-Methoxy Amides and Arynes
Cheng, Xiu-Fen,Yu, Ting,Liu, Yi,Wang, Nan,Chen, Zhenzhen,Zhang, Guang-Lu,Tong, Lili,Tang, Bo
, p. 2087 - 2092 (2022/04/07)
The Pd(II)-catalyzed C-H bond activation/C-N bond cleavage annulation reaction of N-alkyoxyamide aryne is developed to synthesize 9,10-dihydrophenanthrenone derivatives. This reaction exhibited good functional group compatibility with yields up to 92%. Detailed mechanistic studies showed that the key to C-N bond cleavage is the formed eight-membered palladacycle intermediate undergoing nucleophilic addition to the carbonyl group, which provides a new and practical way for N-alkoxyamide directed C-H bond activation.
Direct Heterogenization of the Ru-Macho Catalyst for the Chemoselective Hydrogenation of α,β-Unsaturated Carbonyl Compounds
Padmanaban, Sudakar,Gunasekar, Gunniya Hariyanandam,Yoon, Sungho
supporting information, p. 6881 - 6888 (2021/03/01)
In this study, a commercially available homogeneous pincer-type complex, Ru-Macho, was directly heterogenized via the Lewis acid-catalyzed Friedel-Crafts reaction using dichloromethane as the cross-linker to obtain a heterogeneous, pincer-type Ru porous organometallic polymer (Ru-Macho-POMP) with a high surface area. Notably, Ru-Macho-POMP was demonstrated to be an efficient heterogeneous catalyst for the chemoselective hydrogenation of α,β-unsaturated carbonyl compounds to their corresponding allylic alcohols using cinnamaldehyde as a model compound. The Ru-Macho-POMP catalyst showed a high turnover frequency (TOF = 920 h-1) and a high turnover number (TON = 2750), with high chemoselectivity (99%) and recyclability during the selective hydrogenation of α,β-unsaturated carbonyl compounds.