Immobilization of lipase on Fe3O4/ZnO core/shell magnetic nanoparticles and catalysis of Michael-type addition to chalcone derivatives

Ghasemi, Sabrieh; Heidary, Marjan; Faramarzi, Mohammad Ali; Habibi, Zohreh

doi:10.1016/j.molcatb.2013.12.006

Cited by 42 publications

(24 citation statements)

References 42 publications

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“…Therefore, an appropriate reaction temperature for high yield is of great importance. Lipases have been widely used in Michael reactions between different substrates such as active methylene compounds and chalcones [30], 4-hydroxycoumarin and , -unsaturated enones [31], primary or secondary amines, acrylonitrile, etc. [32].…”

Section: Interactive Effects Of Different Factors On the Lipase/laccamentioning

confidence: 99%

A one‐pot process for synthesis of mitomycin analogs catalyzed by laccase/lipase optimized by response surface methodology

Zhang

Yao

et al. 2019

Engineering in Life Sciences

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To reach the excellent yield as well as environmental friendliness, an efficient one‐pot process for the synthesis of 2‐methyl‐3‐n‐butylaminoyl‐1,4‐benzoquinone, a mitomycin‐like compound by the domino reaction of 2‐methyl‐1,4‐hydroquinone and butylamine using laccase/lipase as co‐catalysts, has been developed. In this present study, the process proposed here was further improved by optimizing the relevant factors using the response surface methodology based on Box–Benkhen Design. The optimum condition that afforded the highest yield (98%) of 2‐methyl‐3‐n‐butylaminoyl‐1,4‐benzoquinone was obtained as follows: molar ratio of amines to hydroquinones 1.16:1, activity ratio of laccase to lipase 1.14:2, and reaction temperature 38.9°C. The results obtained indicate that this process may be useful as a green alternative method for higher yield production of mitomycin analogs.

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Section: Interactive Effects Of Different Factors On the Lipase/laccamentioning

confidence: 99%

A one‐pot process for synthesis of mitomycin analogs catalyzed by laccase/lipase optimized by response surface methodology

Zhang

Yao

et al. 2019

Engineering in Life Sciences

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“…The Michael reaction is one of the most important strategies for the formation of a C─C bond, and it has been widely used to generate valuable building blocks in organic synthesis . It was reported that chalcones were successfully synthesized by the Michael reaction catalyzed by the immobilized Thermomyces lanuginosa lipase (TLL) with the highest yield of 94% . The porcine pancreas lipase (PPL) was employed to mediate the Michael addition of 4‐hydroxycoumarin with α,β‐unsaturated enones inorganic medium to form the anticoagulant Warfarin …”

Section: Introductionmentioning

confidence: 99%

“…3 It was reported that chalcones were successfully synthesized by the Michael reaction catalyzed by the immobilized Thermomyces lanuginosa lipase (TLL) with the highest yield of 94%. 4 The porcine pancreas lipase (PPL) was employed to mediate the Michael addition of 4-hydroxycoumarin with ⊍,⊎-unsaturated enones inorganic medium to form the anticoagulant Warfarin. 5 Mitomycins are antibiotic drugs which have shown strong antineo plastic activity against different cancer models.…”

Section: Introductionmentioning

confidence: 99%

“…14 Amination mediated by laccase proves to be an efficient way which can generate biological active ingredients such as aminonaphthoquinone or aminoquinone derivatives. 15,16 The mitomycin-like compounds such as 5-alkylamino- [1,4]-benzoquinones and 2,5-bis(alkylamino)- [1,4]-benzoquinones, were synthesized by heteromolecular coupling of 2-methoxy-3-methylhydroquinone with primary amines under the catalysis of Myceliophthora thermophile laccase (MtL) and Pycnoporus cinnabarinu laccase (PcL), respectively. 17 The productivity of this process catalyzed by MtL was only 32.9% for monoaminated products as the main product.…”

Section: Introductionmentioning

confidence: 99%

“…reaction (2) and reaction (4). Thus, the integration of the two reactions in the system determined the actual amount of P 3 , which can be seen in Fig.…”

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confidence: 98%

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Synthesis of mitomycin analogs catalyzed by coupling of laccase with lipase and the kinetic model

Zhang

Sun

Ren

et al. 2020

J of Chemical Tech & Biotech

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BACKGROUND Mitomycin C (MMC) is one of the most important members of the mitomycin family that have been widely used as a strong antineoplastic antibiotic for treating various tumors. In this study, enzymatic oxidation/amination reaction of 2‐methyl‐1,4‐hydroquinone with n‐butylamine was carried out to synthesize 2‐methyl‐3‐n‐butylaminoyl‐1,4‐benzoquinone mitomycin analogs. RESULTS A kinetic model was developed based on an ordered sequential mechanism for this cascade reaction system catalyzed by two enzymes, which revealed that the limiting step of the system was the laccase‐mediated oxidation of 2‐methyl‐3‐n‐butylaminoyl‐4‐hydro‐1‐quinone and removing the limiting step resulted in a yield increase from 88.3% to 96.7%. CONCLUSION The developed kinetic model fitted the test data very well, indicating that the reactions catalyzed by coupling of laccase with lipase might follow the ordered sequential mechanism with product inhibition. Synthesis of mitomycin analogs catalyzed by coupling of laccase with lipase has great potential for practical application. © 2020 Society of Chemical Industry

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Aminopropylated PEG as a novel, eco‐friendly and biodegradable basic catalyst for bis‐Michael addition to α,β‐unsaturated ketones under solvent‐free conditions

Khan

Siddiqui

2014

Applied Organom Chemis

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A solvent-free and highly efficient protocol has been developed for the synthesis of novel bis-Michael addition products (3a-o) using aminopropylated PEG-6000 (NH 2 -PEG) as a biodegradable and recyclable catalyst in excellent yields under solvent-free conditions. Other remarkable features of this environmentally benign protocol are shorter reaction time, tolerance of a wide range of C-H-activated acids, high yield of products, and simple experimental and work-up procedure as compared to conventional methods. The NH 2 -PEG catalyst is characterized by using FT-IR, powder XRD and scanning electron microscopyenergy dispersion X-ray spectrometric analyses. The catalyst can be recycled several times without significant loss of its catalytic activity.

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Immobilization of lipase on Fe3O4/ZnO core/shell magnetic nanoparticles and catalysis of Michael-type addition to chalcone derivatives

Cited by 42 publications

References 42 publications

A one‐pot process for synthesis of mitomycin analogs catalyzed by laccase/lipase optimized by response surface methodology

A one‐pot process for synthesis of mitomycin analogs catalyzed by laccase/lipase optimized by response surface methodology

Synthesis of mitomycin analogs catalyzed by coupling of laccase with lipase and the kinetic model

Aminopropylated PEG as a novel, eco‐friendly and biodegradable basic catalyst for bis‐Michael addition to α,β‐unsaturated ketones under solvent‐free conditions

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