Hydrolase-catalyzed Michael addition of imidazoles to acrylic monomers in organic medium

Cai, Ying; Wu, Qi; Xiao, Yihong; Lv, De‐Shui; Lin, Xianfu

doi:10.1016/j.jbiotec.2005.07.001

Cited by 50 publications

(29 citation statements)

References 19 publications

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“…Such products are useful in the treatment of protozoal infections. A more extensive study of this reaction was also reported later [74]. Liu et al, (2008) [75] screened several commercially available lipase preparations for carrying out aza-Markonikov addition of N-heterocycles to vinyl esters in organic solvents.…”

Section: Catalytic Promiscuity In Nearly Anhydrous Organic Solventsmentioning

confidence: 90%

Use of high activity enzyme preparations in neat organic solvents for organic synthesis

Gupta¹,

Mukherjee²,

Malhotra³

2013

Univers Org Chem

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The use of enzymes in nearly anhydrous organic solvents generally results in low initial rates/percentage conversions. The current review focuses on some biocatalyst designs like immobilization on nanomaterials, enzyme precipitated and rinsed with organic solvents (EPROS), crosslinked enzyme crystals (CLEC), crosslinked enzyme aggregates (CLEA), protein coated microcrystals (PCMC) and crosslinked protein coated microcrystals (CLPCMC) which show much better catalytic efficiency in such media as compared to other kinds of biocatalyst preparations. The basic methodology and principle behind these efficient designs are described. The relatively recent results on catalytic promiscuity as seen in low water media have also been covered. It is hoped that this will further encourage wider applications of enzymes in neat organic solvents in organic synthesis.

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Section: Catalytic Promiscuity In Nearly Anhydrous Organic Solventsmentioning

confidence: 90%

Use of high activity enzyme preparations in neat organic solvents for organic synthesis

Gupta¹,

Mukherjee²,

Malhotra³

2013

Univers Org Chem

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“…2006 年该课题 [22] 系统研究了在有机介质中用不同的水解酶催化咪唑及其衍生物与丙烯酸酯的 C -N 键 Michael 加成反应. 发现有 9 种水解酶可以催化 Michael 加成, 由于这些水解酶都属于丝氨酸水解酶家族, 推测水解酶催化 Michael 加成可能发生在水解酶的催化活性中心.…”

Section: 水解酶非专一性催化在有机合成中的应用unclassified

Application of Hydrolase Catalytic Promiscuity in Organic Synthesis

Ge¹,

Lai²,

Chen³

2013

Chin. J. Org. Chem.

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“…[33] However, lipases are not the only hydrolases that can be used as promiscuous catalysts in Michael-type additions. For instance, the group of Lin reported the protease from Bacillus subtilis as catalyst for Michael-type additions of imidazoles to acrylic monomers, [34] and also pyrimidine derivatives to ethylenic compounds. [35] Once we had demonstrated the catalytic usefulness of Alcalase-CLEA in the creation of C À C bonds, we moved forward trying to expand its catalytic possibilities and investigating its behaviour as catalyst in C À N bond forming reactions.…”

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confidence: 99%

Use of Protease from Bacillus licheniformis as Promiscuous Catalyst for Organic Synthesis: Applications in CC and CN Bond Formation Reactions

et al. 2011

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Commercially available protease from Bacillus licheniformis has been used in different non-conventional biotransformations showing remarkable activity values. The promiscuous behaviour of this enzyme used in the cross-linked enzyme aggregates immobilized form (Alcalase-CLEA ), has been successfully demonstrated for the first time in C À C bond formation processes such as aldol, Henry and Mannich reactions. On the other hand, the Bayllis-Hillman reaction between 4-nitrobenzaldehyde and methyl vinyl ketone occurred through unspecific catalysis. Interestingly, azaMichael addition reactions of secondary amines (di-A C H T U N G T R E N N U N G ethylamine, piperidine and pyrrolidine) to acrylonitrile have been also efficiently catalyzed, observing with diethylamine the most remarkable differences between the enzyme-mediated reaction and the one in the absence of catalyst. Higher reactivities were attained with pyrrolidine demonstrating the versatility of hydrolases in organic synthesis.

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Hydrolase-catalyzed Michael addition of imidazoles to acrylic monomers in organic medium

Cited by 50 publications

References 19 publications

Use of high activity enzyme preparations in neat organic solvents for organic synthesis

Use of high activity enzyme preparations in neat organic solvents for organic synthesis

Application of Hydrolase Catalytic Promiscuity in Organic Synthesis

Use of Protease from Bacillus licheniformis as Promiscuous Catalyst for Organic Synthesis: Applications in CC and CN Bond Formation Reactions

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