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74-89-5Relevant articles and documents
A Plausible Prebiotic Origin of Glyoxylate: Nonenzymatic Transamination Reactions of Glycine with Formaldehyde
Mohammed, Fiaz S.,Chen, Ke,Mojica, Mike,Conley, Mark,Napoline, Jonathan W.,Butch, Christopher,Pollet, Pamela,Krishnamurthy, Ramanarayanan,Liotta, Charles L.
, p. 93 - 97 (2017)
Glyoxylate has been postulated to be an important prebiotic building block. However, a plausible prebiotic availability of glyoxylate has not as yet been demonstrated. Herein we report the formation of glyoxylate by means of a transamination reaction between glycine and formaldehyde in water at 50 °C and 70 °C at pH 8 and 6, respectively. The reaction was followed by means of 13C NMR and high-resolution mass spectrometry employing both unlabeled and 13C-labeled reactants. Other products accompanying the transamination process include serine, sarcosine, N,N-dimethylglycine, and carbon dioxide/bicarbonate. The mechanisms for the formation of glyoxylate and accompanying products are discussed. 1 Introduction 2 Background 3 Results and Discussion 3.1 Reaction of 13C-Labeled Glycine with Formaldehyde at pH 8 3.2 Reaction of 13C-Labeled Glycine with Formaldehyde at pH 6 3.3 Serine-Promoted Decarboxylation of Glyoxylate 4 Conclusions.
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Romburgh
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Pallazzo,Marogna
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Kohin,Nadeau
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Trillat,Fayollet
, p. 23 (1894)
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Aston,Hu
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Samuelsen et al.
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Schuerc, C.,Huntress, E. H.
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An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes
Lin, Yutong,Malins, Lara R.
supporting information, p. 11811 - 11819 (2021/08/16)
Designer C-terminal peptide amides are accessed in an efficient and epimerization-free approach by pairing an electrochemical oxidative decarboxylation with a tandem hydrolysis/reduction pathway. Resembling Nature's dual enzymatic approach to bioactive primary α-amides, this method delivers secondary and tertiary amides bearing high-value functional motifs, including isotope labels and handles for bioconjugation. The protocol leverages the inherent reactivity of C-terminal carboxylates, is compatible with the vast majority of proteinogenic functional groups, and proceeds in the absence of epimerization, thus addressing major limitations associated with conventional coupling-based approaches. The utility of the method is exemplified through the synthesis of natural product acidiphilamide A via a key diastereoselective reduction, as well as bioactive peptides and associated analogues, including an anti-HIV lead peptide and blockbuster cancer therapeutic leuprolide.
Electrochemical Reductive N-Methylation with CO2Enabled by a Molecular Catalyst
Rooney, Conor L.,Wu, Yueshen,Tao, Zixu,Wang, Hailiang
supporting information, p. 19983 - 19991 (2021/12/01)
The development of benign methylation reactions utilizing CO2 as a one-carbon building block would enable a more sustainable chemical industry. Electrochemical CO2 reduction has been extensively studied, but its application for reductive methylation reactions remains out of the scope of current electrocatalysis. Here, we report the first electrochemical reductive N-methylation reaction with CO2 and demonstrate its compatibility with amines, hydroxylamines, and hydrazine. Catalyzed by cobalt phthalocyanine molecules supported on carbon nanotubes, the N-methylation reaction proceeds in aqueous media via the chemical condensation of an electrophilic carbon intermediate, proposed to be adsorbed or near-electrode formaldehyde formed from the four-electron reduction of CO2, with nucleophilic nitrogenous reactants and subsequent reduction. By comparing various amines, we discover that the nucleophilicity of the amine reactant is a descriptor for the C-N coupling efficacy. We extend the scope of the reaction to be compatible with cheap and abundant nitro-compounds by developing a cascade reduction process in which CO2 and nitro-compounds are reduced concurrently to yield N-methylamines with high monomethylation selectivity via the overall transfer of 12 electrons and 12 protons.
MOF-Derived Cu-Nanoparticle Embedded in Porous Carbon for the Efficient Hydrogenation of Nitroaromatic Compounds
Qiao, Chenxia,Jia, Wenlan,Zhong, Qiming,Liu, Bingyu,Zhang, Yifu,Meng, Changgong,Tian, Fuping
, p. 3394 - 3401 (2020/05/19)
Abstract: Novel Cu-nanoparticles (NPs) embedded in porous carbon materials (Cu@C-x) were prepared by one-pot pyrolysis of metal–organic frameworks (MOF) HKUST-1 at different temperatures. The obtained material Cu@C-x was used as a cost-effective catalyst for the hydrogenation of nitrobenzene using NaBH4 as the reducing agent under mild reaction conditions. By considering the catalyst preparation and the catalytic activity, a pyrolysis temperature of 400?°C was finally chosen to synthesize the optimal catalyst. When the aromatic nitro compounds with reducible groups, such as cyano, halogen, and alkyl groups, were tested in this catalytic hydrogenation, an excellent selectivity approaching 100% was achieved. In the recycling experiment, a significant decrease in nitrobenzene conversion was observed in the third cycle, mainly due to the very small amount of catalyst employed in the reaction. Hence, the easily prepared and cost-effective Cu@C-400 catalyst fabricated in this study demonstrates potential for the applications in selective reduction of aromatic nitro compounds. Graphic Abstract: The catalyst Cu@C-400 exhibited 100?% conversion and high selectivity for the hydrogenation of industrially relevant nitroarenes.[Figure not available: see fulltext.].