Highly efficient and large-scalable glucoamylase-catalyzed Henry reactions

Gao, Na; Chen, Yanli; He, Yan‐Hong; Guan, Zhi

doi:10.1039/c3ra41287c

Cited by 23 publications

(11 citation statements)

References 38 publications

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“…The reactions were carried out at room temperature, and the corresponding nitroalcohols were obtained in yields up to 96%. Then, the same group reported glucoamylase from Aspergillus niger (AnGA) catalyze Henry reactions of aromatic aldehydes and nitroalkanes in 2013 [50]. The reactions were carried out at 30°C in the mixed solvents of ethanol and water, and the corresponding β-nitro alcohols were obtained in yields of up to 99%.…”

Section: Henry (Nitroaldol) Reactionmentioning

confidence: 99%

Hydrolase-Catalyzed Promiscuous Reactions and Applications in Organic Synthesis

Wang¹,

Wang²

2021

Molecular Biotechnology

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The potential of biocatalysis becomes increasingly recognized as an efficient and green tool for modern organic synthesis. Biocatalytic promiscuity, a new frontier extended the use of enzymes in organic synthesis, has attracted much attention and expanded rapidly in the past decade. It focuses on the enzyme catalytic activities with unnatural substrates and alternative chemical transformations. Exploiting enzyme catalytic unconventional reactions might lead to improvements in existing catalysts and provide novel synthesis pathways that are currently not available. Among these enzymes, hydrolase (such as lipase, protease, acylase) undoubtedly has received special attention since they display remarkable activities for some unexpected reactions such as aldol reaction and other novel carbon-carbon and carbon-heteroatom bond-forming reactions. This chapter introduces the recent progress in hydrolase catalytic unconventional reactions and application in organic synthesis. Some important examples of hydrolase catalytic unconventional reactions in addition reactions are reviewed, highlighting the catalytic promiscuity of hydrolases focuses on aldol reaction, Michael addition, and multicomponent reactions.

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Section: Henry (Nitroaldol) Reactionmentioning

confidence: 99%

Hydrolase-Catalyzed Promiscuous Reactions and Applications in Organic Synthesis

Wang¹,

Wang²

2021

Molecular Biotechnology

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“…Henry reactions allow the preparation of α,β‐nitro alcohols by reacting a carbonyl compound and an alkyl nitro compound. When Henry reactions between aromatic aldehydes 9 and nitroalkanes 10 catalyzed by glucoamylase from Aspergillus niger (AnGA) were carried out at 30 °C in ethanol, the yield of β‐nitro alcohols 11 was raised from 87% to 99% as the water content increased from 0 to 0.15 (Scheme ) …”

Section: Effect Of Water Moleculesmentioning

confidence: 99%

Effect of Additives on the Selectivity and Reactivity of Enzymes

Liang

Lin

2016

Chem. Rec.

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Enzymes have been widely used as efficient, eco-friendly, and biodegradable catalysts in organic chemistry due to their mild reaction conditions and high selectivity and efficiency. In recent years, the catalytic promiscuity of many enzymes in unnatural reactions has been revealed and studied by chemists and biochemists, which has expanded the application potential of enzymes. To enhance the selectivity and activity of enzymes in their natural or promiscuous reactions, many methods have been recommended, such as protein engineering, process engineering, and media engineering. Among them, the additive approach is very attractive because of its simplicity to use and high efficiency. In this paper, we will review the recent developments about the applications of additives to improve the catalytic performances of enzymes in their natural and promiscuous reactions. These additives include water, organic bases, water mimics, cosolvents, crown ethers, salts, surfactants, and some particular molecular additives.

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Section: Carbon–carbon Bond‐formation Reactionsmentioning

confidence: 99%

“…In addition, other hydrolases such as glucoamylase from Aspergillus niger (AnGA) and a D ‐aminoacylase have also been found to catalyze the Henry reaction. A large and scalable AnGA‐catalyzed Henry reaction has been described between (hetero)aromatic aldehydes and nitroalkanes (5 equiv) such as nitromethane, nitroethane and nitropropane in a mixture of ethanol and water (85:15 v/v) at an optimum temperature of 30°C . The specific catalytic activity of AnGA in the Henry reaction was nicely demonstrated by a rational design of experiments including the presence of possible inhibitors such as metal ions (Ag + and Cu 2+ ) or miglitol, and also denaturation reagents such as urea or guanidine.…”

Section: Carbon–carbon Bond‐formation Reactionsmentioning

confidence: 99%

Recent Advances in Biocatalytic Promiscuity: Hydrolase‐Catalyzed Reactions for Nonconventional Transformations

López-Iglesias

Gotor‐Fernández

2015

The Chemical Record

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Enzymes has emerged in recent decades as ideal catalysts for synthetic transformations in mild reaction conditions. Their capacity to accelerate a myriad of biotransformations with high levels of selectivity and broad substrate specificity including excellent atom economy has led to a current full recognition. The six classes of enzymes (oxidoreductases, transferases, hydrolases, lyases, isomerases and ligases) possess outstanding abilities to perform specific modifications in target molecules. Nevertheless, in the last fifteen years, novel examples have appeared related to nonconventional processes catalyzed by various classes of biocatalysts. Amongst these, hydrolases have received special attention since they display remarkable activities in initially unexpected reactions such as carbon-carbon and carbon-heteroatom bond formation reactions, oxidative processes and novel hydrolytic transformations. In this review, the main findings in this area will be disclosed, highlighting the catalytic properties of hydrolases not only to catalyze single processes but also multicomponent and tandem nonconventional reactions.

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Highly efficient and large-scalable glucoamylase-catalyzed Henry reactions

Cited by 23 publications

References 38 publications

Hydrolase-Catalyzed Promiscuous Reactions and Applications in Organic Synthesis

Hydrolase-Catalyzed Promiscuous Reactions and Applications in Organic Synthesis

Effect of Additives on the Selectivity and Reactivity of Enzymes

Recent Advances in Biocatalytic Promiscuity: Hydrolase‐Catalyzed Reactions for Nonconventional Transformations

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