Recent advances in multicomponent reactions involving carbohydrates
TL;DR: The advances in the synthesis of structurally diversified sugar-based derivatives through new multicomponent reactions of the previous decade are reviewed in this paper, where the authors present a review of the progress in this area.
Abstract: Being an attractive class of naturally occurring molecules with fascinating properties sugars and their derivatives have wide applications in different fields especially in drug discovery. Due to their highly diverse nature they play various important key roles in biological systems. In terms of providing both desirable structural diversity and compound libraries, multicomponent reactions (MCRs) are most efficient strategies. MCRs are widely employed by chemists to generate sugar based derivatives with significantly extended variations having various benefits to society. The advances in the synthesis of structurally diversified sugar based derivatives through new MCRs of the previous decade are reviewed.
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TL;DR: In this article, the effects of electron donating (−CH3 and −OH) and electron withdrawing (−NO2) substituents on the corrosion inhibition efficiency of four glucosamine-based, substituted, pyrimidine-fused heterocycles (CARBs) on mild steel corrosion in 1 M HCl have been investigated using gravimetric, electrochemical, surface morphology (SEM, AFM, and EDX), and computational techniques.
Abstract: Effects of electron donating (−CH3 and −OH) and electron withdrawing (−NO2) substituents on the corrosion inhibition efficiency of four glucosamine-based, substituted, pyrimidine-fused heterocycles (CARBs) on mild steel corrosion in 1 M HCl have been investigated using gravimetric, electrochemical, surface morphology (SEM, AFM, and EDX), and computational techniques. Gravimetric studies showed that protection performances of the compounds increase with increase in concentration. Both electron withdrawing (−NO2) and electron donating (−CH3 and −OH) groups were found to enhance the inhibition efficiency, but the effect is more pronounced with electron-donating substituents. The compounds were found to be cathodic-type inhibitors as inferred from the results of potentiodynamic polarization studies. EIS studies suggested that the studied compounds inhibit metallic corrosion by adsorbing on metallic surface. The adsorption of the inhibitor molecules on steel surface was further supported by SEM, AFM, and EDX a...
385 citations
TL;DR: Polarization study suggests that the studied compounds are mixed-type but exhibited predominantly cathodic inhibitive effect, and adsorption of these compounds on mild steel surface obeyed the Langmuir adsorptive isotherm.
Abstract: D-glucose derivatives of dihydropyrido-[2,3-d:6,5-d′]-dipyrimidine-2, 4, 6, 8(1H,3H, 5H,7H)-tetraone (GPHs) have been synthesized and investigated as corrosion inhibitors for mild steel in 1M HCl solution using gravimetric, electrochemical, surface, quantum chemical calculations and Monte Carlo simulations methods. The order of inhibition efficiencies is GPH-3 > GPH-2 > GPH-1. The results further showed that the inhibitor molecules with electron releasing (-OH, -OCH3) substituents exhibit higher efficiency than the parent molecule without any substituents. Polarization study suggests that the studied compounds are mixed-type but exhibited predominantly cathodic inhibitive effect. The adsorption of these compounds on mild steel surface obeyed the Langmuir adsorption isotherm. SEM, EDX and AFM analyses were used to confirm the inhibitive actions of the molecules on mild steel surface. Quantum chemical (QC) calculations and Monte Carlo (MC) simulations studies were undertaken to further corroborate the experimental results.
135 citations
TL;DR: In peptide chemistry, the versatility of the multicomponent ligation strategy is demonstrated in both solution-phase lipidation protocols and solid-phase procedures enabling the simultaneous lipidation and biotinylation of peptides, and it is shown that MCRs are powerful methods for synchronized lipidation/labeling and macrocyclization of peptide, thus accomplishing in one step what usually requires long sequences.
Abstract: ConspectusMulticomponent reactions (MCRs) encompass an exciting class of chemical transformations that have proven success in almost all fields of synthetic organic chemistry. These convergent procedures incorporate three or more reactants into a final product in one pot, thus combining high levels of complexity and diversity generation with low synthetic cost. Striking applications of these processes are found in heterocycle, peptidomimetic, and natural product syntheses. However, their potential in the preparation of large macro- and biomolecular constructs has been realized just recently. This Account describes the most relevant results of our group in the utilization of MCRs for ligation/conjugation of biomolecules along with significant contributions from other laboratories that validate the utility of this special class of bioconjugation process. Thus, MCRs have proven to be efficient in the ligation of lipids to peptides and oligosaccharides as well as the ligation of steroids, carbohydrates, and f...
84 citations
TL;DR: In this paper, cycloamination approaches for thermal (catalyst-free) and catalytic transformation of biomass feedstocks into N-heterocyclic molecules including mechanistic pathways are analyzed.
81 citations
TL;DR: The metal-catalyzed multicomponent reactions (MCRs) are versatile synthetic protocols frequently utilized in the preparation of numerous natural products and pharmaceuticals, offering perfect molecular diversity and high level of atom efficiency with energy saving in a single reaction step as mentioned in this paper.
58 citations
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TL;DR: The only common features of the varied functions of oligosaccharides are that they either mediate ‘specific recognition’ events or that they provide ‘modulation’ of biological processes.
Abstract: Many different theories have been advanced concerning the biological roles of the oligosaccharide units of individual classes of glycoconjugates. Analysis of the evidence indicates that while all of these theories are correct, exceptions to each can also be found. The biological roles of oligosaccharides appear to span the spectrum from those that are trivial, to those that are crucial for the development, growth, function or survival of an organism. Some general principles emerge. First, it is difficult to predict a priori the functions a given oligosaccharide on a given glycoconjugate might be mediating, or their relative importance to the organism. Second, the same oligosaccharide sequence may mediate different functions at different locations within the same organism, or at different times in its ontogeny or life cycle. Third, the more specific and crucial biological roles of oligosaccharides are often mediated by unusual oligosaccharide sequences, unusual presentations of common terminal sequences, or by further modifications of the sugars themselves. However, such oligosaccharide sequences are also more likely to be targets for recognition by pathogenic toxins and microorganisms. As such, they are subject to more intra- and inter-species variation because of ongoing host-pathogen interactions during evolution. In the final analysis, the only common features of the varied functions of oligosaccharides are that they either mediate 'specific recognition' events or that they provide 'modulation' of biological processes. In so doing, they generate much of the functional diversity required for the development and differentiation of complex organisms, and for their interactions with other organisms in the environment.
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3,909 citations
TL;DR: Eutectic mixtures of urea and a range of quaternary ammonium salts are liquid at ambient temperatures and have interesting solvent properties.
3,550 citations
TL;DR: All works discussed in this review aim at demonstrating that Deep Eutectic Solvents not only allow the design of eco-efficient processes but also open a straightforward access to new chemicals and materials.
Abstract: Within the framework of green chemistry, solvents occupy a strategic place. To be qualified as a green medium, these solvents have to meet different criteria such as availability, non-toxicity, biodegradability, recyclability, flammability, and low price among others. Up to now, the number of available green solvents are rather limited. Here we wish to discuss a new family of ionic fluids, so-called Deep Eutectic Solvents (DES), that are now rapidly emerging in the current literature. A DES is a fluid generally composed of two or three cheap and safe components that are capable of self-association, often through hydrogen bond interactions, to form a eutectic mixture with a melting point lower than that of each individual component. DESs are generally liquid at temperatures lower than 100 °C. These DESs exhibit similar physico-chemical properties to the traditionally used ionic liquids, while being much cheaper and environmentally friendlier. Owing to these remarkable advantages, DESs are now of growing interest in many fields of research. In this review, we report the major contributions of DESs in catalysis, organic synthesis, dissolution and extraction processes, electrochemistry and material chemistry. All works discussed in this review aim at demonstrating that DESs not only allow the design of eco-efficient processes but also open a straightforward access to new chemicals and materials.
3,325 citations
Journal Article•
TL;DR: Chemical tools have proven indispensable for studies in glycobiology and chemical approaches are contributing great insight into the myriad biological functions of oligosaccharides.
Abstract: Chemical tools have proven indispensable for studies in glycobiology. Synthetic oligosaccharides and glycoconjugates provide materials for correlating structure with function. Synthetic mimics of the complex assemblies found on cell surfaces can modulate cellular interactions and are under development as therapeutic agents. Small molecule inhibitors of carbohydrate biosynthetic and processing enzymes can block the assembly of specific oligosaccharide structures. Inhibitors of carbohydrate recognition and biosynthesis can reveal the biological functions of the carbohydrate epitope and its cognate receptors. Carbohydrate biosynthetic pathways are often amenable to interception with synthetic unnatural substrates. Such metabolic interference can block the expression of oligosaccharides or alter the structures of the sugars presented on cells. Collectively, these chemical approaches are contributing great insight into the myriad biological functions of oligosaccharides.
1,128 citations