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Efficient synthesis of the key chiral alcohol intermediate of Crizotinib using dual-enzyme@CaHPO4 hybrid nanoflowers assembled by mimetic biomineralization

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논문

Efficient synthesis of the key chiral alcohol intermediate of Crizotinib using dual-enzyme@CaHPO4 hybrid nanoflowers assembled by mimetic biomineralization

학술지

Journal of chemical technology and biotechnology

저자명

Chen, Xinxin; Xu, Liqing; Wang, Anming; Li, Huimin; Wang, Chenhui; Pei, Xiaolin; Zhang, Pengfei; Wu, Stephen G

초록

<P><B>Abstract</B></P><P><B>BACKGROUND</B></P><P>To develop an environment&#8208;friendly approach for the synthesis of (S)&#8208;1&#8208;(2,6&#8208;dichloro&#8208;3&#8208;fluorophenyl) ethyl alcohol, an intermediate of anti&#8208;cancer drug Crizotinib, aldehyde ketone reductase and alcohol dehydrogenase were overexpressed in <I>Escherichia coli</I> Rosetta (DE3) and purified via chromatography. Subsequently, they were co&#8208;crystalized with CaHPO<SUB>4</SUB> at 4&deg;C to form dual&#8208;enzyme@CaHPO<SUB>4</SUB> hybrid nanoflowers (hNFs) which was then used to catalyze the synthesis of (S)&#8208;1&#8208;(2,6&#8208;dichloro&#8208;3&#8208;fluorophenyl) ethyl alcohol along with the evaluation of its thermal stability and recycling stability.</P><P><B>RESULTS</B></P><P>At optimum pH of 7.0, the activities of AKR and ADH confined in the dual&#8208;enzyme@CaHPO<SUB>4</SUB> hybrid nanoflowers were 3.3&#8208; and 2.1&#8208;fold that of the corresponding free one. The thermos&#8208;stability of confined enzymes was also significantly improved: both enzymes within the hNFs remained more than 80% of initial activities after incubation at 60&deg;C for 8 h, while free enzymes only retained 20% of initial activities under the same treatment conditions. Moreover, AKR and ADH immobilized with a mole ratio of 3:1 confined in hybrid nanoflowers exhibited the highest catalytic activity for the synthesis of chiral ethyl alcohol with a yield up to 90.8% after 12 h. Besides, the final product (S)&#8208;1&#8208;(2,6&#8208;dichloro&#8208;3&#8208;fluorophenyl) ethyl alcohol showed a high ee value of 99.99%. Further, the hybrid nanoflowers retained their initial activity after 16 recycling cycles of synthesis reaction.</P><P><B>CONCLUSION</B></P><P>The dual&#8208;enzyme@CaHPO<SUB>4</SUB> hybrid nanoflowers efficiently catalyzed synthesis of the chiral compound (S)&#8208;1&#8208;(2,6&#8208;dichloro&#8208;3&#8208;fluorophenyl) ethyl alcohol. The method can also be applied to other multi&#8208;enzyme systems and facilitate their cascade reactions and substrate channeling. &copy; 2018 Society of Chemical Industry</P>

발행연도

2019

발행기관

John WileySons, Ltd.

ISSN

0268-2575

ISSN

1097-4660

94

1

페이지

pp.236-243

주제어

Crizotinib; dual&#x2010; enzyme@CaHPO4 hybrid nanoflowers; chiral alcohol; cascade reaction;

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논문; 2019-12-31

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