Investigations on enzyme catalytic promiscuity: The first attempts at a hydrolytic enzyme-promoted conjugate addition of nucleophiles to α,β-unsaturated sulfinyl acceptors

Madalińska, Lidia; Kwiatkowska, Małgorzata; Cierpiał, Tomasz; Kiełbasiński, P.

doi:10.1016/j.molcatb.2012.05.002

Cited by 15 publications

(10 citation statements)

References 38 publications

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“…Numerous examples pertain to the stereoselective synthesis of chiral intermediates for the production of various pharmaceuticals and plant-protecting agents (Andualema & Gessesse, 2012;Baldessari, 2012;Naik et al, 2010;Sharma et al, 2011;Song et al, 2008). Moreover, there are many cases of promiscuous reactions catalyzed by CAL-B, including aldol reactions, Michael additions, vinyl polymerization, and even oxidations (Branneby et al, 2004;Carboni-Oerlemans et al, 2006;Carlqvist et al, 2003;Carlqvist et al, 2005;Hult & Berglund, 2007;Madalińska et al, 2012;Rustoy et al, 2007;Sharma et al, 2009;Svedendahl et al, 2005;Wu et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Crystal and molecular structure of hexagonal form of lipase B from Candida antarctica.

Strzelczyk¹,

Bujacz²,

Kiełbasiński³

et al. 2015

Acta Biochim Pol

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During crystallization screenings of commercially available hydrolytic enzymes, the new, hexagonal crystal form of CAL-B, has been discovered and hereby reported. The NAG molecules, which were closing the glycosylation site in the orthorhombic form, in hexagonal structure make the glycosylation site open. It is unknown whether the opening and closing of the glycosylation site by the 'lid' NAG molecules, could be related to the opening and closing of the active center of the enzyme upon substrate binding and product release.

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Section: Introductionmentioning

confidence: 99%

Crystal and molecular structure of hexagonal form of lipase B from Candida antarctica.

Strzelczyk¹,

Bujacz²,

Kiełbasiński³

et al. 2015

Acta Biochim Pol

Self Cite

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“…We design a magnetic nanoparticles-based catalytic The aza-Michael addition reaction of acryl amides is significant for preparing kinds of β-amino carbonyl compounds from readily manufactured raw materials in a sustainable and clean method [41][42][43][44][45][46]. Recently, the researches in aza-Michael addition by the imidazolium-based polymer [47], enzymes [48][49][50][51], and room-temperature ionic liquids (RTILs) have given a novelty way to achieve the important β-amino carbonyl derivatives [28]. These methods definitely have excellent potential as powerful tools which can build multiple molecules with different acryl amides, and in the meantime provide new catalytic cascade reaction sequences.…”

Section: Resultsmentioning

confidence: 99%

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Liu

Luo

et al. 2017

Catalysts

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Abstract:A nanostructure-based catalytic system has the advantages of both homogeneous and heterogeneous catalysis. It is of great significance to develop the sustainable and green process of homogeneous catalytic reaction. We report a novel, efficient and recyclable magnetic Fe 3 O 4 nanoparticles-catalyzed aza-Michael addition reaction of acryl amides, and the magnetic nanoparticles catalysts can be recovered by external magnetic field. Both primary amine and secondary amine can react with various acryl amides providing a good output to target products successfully at room temperature. Further experiments reveal that the magnetic Fe 3 O 4 nanoparticles-based catalyst shows excellent yields, which can be recycled 10 times, and, at the same time, it maintains a high catalytically activity. In this catalytic system, the tedious separation procedures are replaced by external magnetic field, which gives us a different direction for choosing a catalyst in a nanostructure-based catalytic system.

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“…The biocatalytic thia-Michael reaction is an attractive strategy to develop C▬S bond-forming reactions. In 2012, Kiełbasinski and co-workers have reported the use of a number of lipases including PPL, MJL, CALB, and PSL in the addition of benzenethiol to racemic phenyl vinyl sulfoxide or 2-phosphono-2,3didehydrothiolane S-oxide in organic solvents at room temperature ( Figure 15) [28]. The addition of piperidine to phenyl vinyl sulfoxide in chloroform is carried out in both enzymatic and non-catalytic processes, while in the former, the reaction rate is 2.5 times faster.…”

Section: Carbon-heteroatom Bond Formation Michael Additionmentioning

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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Investigations on enzyme catalytic promiscuity: The first attempts at a hydrolytic enzyme-promoted conjugate addition of nucleophiles to α,β-unsaturated sulfinyl acceptors

Cited by 15 publications

References 38 publications

Crystal and molecular structure of hexagonal form of lipase B from Candida antarctica.

Crystal and molecular structure of hexagonal form of lipase B from Candida antarctica.

Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field

Hydrolase-Catalyzed Promiscuous Reactions and Applications in Organic Synthesis

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