One-Pot Construction of Diverse β-Lactam Scaffolds via the Green Oxidation of Amines and Its Application to the Diastereoselective Synthesis of β-Amino Acids

Yamamoto, Yuki; Kodama, Shintaro; Nishimura, Riku; Nomoto, Akihiro; Ueshima, Michio

doi:10.1021/acs.joc.1c01128

Cited by 18 publications

(6 citation statements)

References 87 publications

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“…Enzymes are powerful catalysts, but they are also very delicate molecules that can easily be denaturated beyond their normal environment. The application of one-step synthesis in producing polymer scaffolds has been reported in imidazole scaffolds [ 157 ], porous membrane-based scaffolds [ 158 ], multiple heterocyclic scaffolds [ 159 ], and the construction of β-Lactam scaffolds [ 160 ]. The successful fusion of enzymes with adaptable synthetic or natural polymers is made possible by a variety of opportunities provided by polymer chemistry, which can help resolve this problem.…”

Section: One-step Synthesis Applicationmentioning

confidence: 99%

Advances in the One-Step Approach of Polymeric Materials Using Enzymatic Techniques

et al. 2023

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The formulation in which biochemical enzymes are administered in polymer science plays a key role in retaining their catalytic activity. The one-step synthesis of polymers with highly sequence-controlled enzymes is a strategy employed to provide enzymes with higher catalytic activity and thermostability in material sustainability. Enzyme-catalyzed chain growth polymerization reactions using activated monomers, protein–polymer complexation techniques, covalent and non-covalent interaction, and electrostatic interactions can provide means to develop formulations that maintain the stability of the enzyme during complex material processes. Multifarious applications of catalytic enzymes are usually attributed to their efficiency, pH, and temperature, thus, progressing with a critical structure-controlled synthesis of polymer materials. Due to the obvious economics of manufacturing and environmental sustainability, the green synthesis of enzyme-catalyzed materials has attracted significant interest. Several enzymes from microorganisms and plants via enzyme-mediated material synthesis have provided a viable alternative for the appropriate synthesis of polymers, effectively utilizing the one-step approach. This review analyzes more and deeper strategies and material technologies widely used in multi-enzyme cascade platforms for engineering polymer materials, as well as their potential industrial applications, to provide an update on current trends and gaps in the one-step synthesis of materials using catalytic enzymes.

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Section: One-step Synthesis Applicationmentioning

confidence: 99%

Advances in the One-Step Approach of Polymeric Materials Using Enzymatic Techniques

et al. 2023

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“…The implementation process is more complicated. Carrying out good landscape design is of great importance and positive significance for improving the level of urban habitat and achieving a double harvest of local material and spiritual civilization [7][8][9]. Notteboom et al analyzed the role of gardens and green spaces in cities in different eras, summarized the themes of garden design in different stages, and proposed relevant recommendations and measures to promote the development of garden design [10].…”

Section: Introductionmentioning

confidence: 99%

Modern garden design thinking and practice based on spatial information technology

Yang

2023

Applied Mathematics and Nonlinear Sciences

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The construction of a garden image classification model is done by combining spatial information technology and analyzing the process of hyperspectral classification of garden images is the main focus of this paper. The linear transformation of the image is performed by principal component analysis to achieve the effect of reducing image dimension. The SVM classifier is used to classify the garden images, and the hyperplane is found in the sample space to distinguish between positive and negative cases. Using a simple linear iterative algorithm, the image superpixels are segmented, and the information contained in them is fused with the features of the hyperspectral image. The positioning of the hyperpixel block impacts the calculation of the mean hyperspectral feature value for each hyperpixel region. The results show that a well-rounded designer needs to achieve 70% aesthetics and 80% rationality to present modern garden design.

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“…In addition, unstable imines can be easily prepared and used directly for the one-pot synthesis of various functional molecules, thus providing a series of innovative catalytic oxidation processes. This metal-free imine synthesis method not only enables the one-pot synthesis of important heterocyclic compounds, but also the highly selective one-pot reactions (e.g., the Ugi reaction) of multicomponent linkages ( Dong, et al, 2017 ; Kumazawa, et al, 2018 ; Dong et al, 2019 ; Yamamoto et al, 2021 ). To further elucidate the versatility of this metal-free imine synthesis method, we attempted one-pot synthesis for reactions that are typically multistep, and succeeded in the metal-free synthesis of quinazoline derivatives ( Wang and Gao, 2013 ; Faisal and Saeed, 2021 ), which are one of the heterocycles forming the basis of pharmaceuticals, agrochemicals, and functional materials (eq 2).…”

Section: Introductionmentioning

confidence: 99%

Metal-Free Synthesis of 2-Substituted Quinazolines via Green Oxidation of o-Aminobenzylamines: Practical Construction of N-Containing Heterocycles Based on a Salicylic Acid-Catalyzed Oxidation System

et al. 2022

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Conventional quinazoline synthesis methods involve a highly multistep reaction, and often require excess amounts of substrate to control the product selectivity, leading to significant resource wastage. Hence, in this study, from the viewpoint of green chemistry, we developed a novel metal-free synthetic method for 2-substituted quinazoline derivatives by the 4,6-dihydroxysalicylic acid-catalyzed oxidative condensation of o-aminobenzylamines and benzylamines using atmospheric oxygen. In this system, the use of a catalytic amount of BF3‧Et2O (10 mol%) as a Lewis acid successfully led to the efficient oxidative condensation and intramolecular cyclization of these amines, followed by aromatization to afford the corresponding 2-arylquinazolines in up to 81% yield with excellent atom economy and environmental factor. Furthermore, to expand this green oxidation method to gram-scale synthesis, we investigated the development of an oxidation process using salicylic acid itself as an organocatalyst, and established a method for the practical green synthesis of a series of nitrogen-containing heterocycles. We expect that the findings will contribute to the development of practical synthesis methods for pharmaceutical manufacturing and industrial applications, along with further advancements in green chemistry.

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One-Pot Construction of Diverse β-Lactam Scaffolds via the Green Oxidation of Amines and Its Application to the Diastereoselective Synthesis of β-Amino Acids

Cited by 18 publications

References 87 publications

Advances in the One-Step Approach of Polymeric Materials Using Enzymatic Techniques

Advances in the One-Step Approach of Polymeric Materials Using Enzymatic Techniques

Modern garden design thinking and practice based on spatial information technology

Metal-Free Synthesis of 2-Substituted Quinazolines via Green Oxidation of o-Aminobenzylamines: Practical Construction of N-Containing Heterocycles Based on a Salicylic Acid-Catalyzed Oxidation System

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