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Designing of a cofactor self-sufficient whole-cell biocatalyst system for production of 1,2-amino alcohols from epoxides

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논문

Designing of a cofactor self-sufficient whole-cell biocatalyst system for production of 1,2-amino alcohols from epoxides

학술지

ACS Synthetic biology

저자명

Liu, Song; Zhang, Xian; Liu, Fei; Xu, Meijuan; Yang, Taowei; Long, Mengfei; Zhou, Junping; Osire, Tolbert; Yang, Shangtian; Rao, Zhiming

초록

<P>Optically pure 1,2-amino alcohols are highly valuable products as intermediates for chiral pharmaceutical products. Here we designed an environmentally friendly non-natural biocatalytic cascade for efficient synthesis of 1,2-amino alcohols from cheaper epoxides. A redesignated &omega;-transaminase PAK&omega;-TA was tested and showed good bioactivity at a lower pH than other reported transaminases. The cascade was efficiently constructed as a single one-pot <I>E. coli</I> recombinant, by coupling SpEH (epoxide hydrolase), MnADH (alcohol dehydrogenase), and PAK&omega;-TA. Furthermore, RBS regulation strategy was used to overcome the rate limiting step by increasing expression of MnADH. For cofactor regeneration and amino donor source, an interesting point was involved as that a cofactor self-sufficient system was designed by expression of GluDH. It established a “bridge” between the cofactor and the cosubstrate, such that the cofactor self-sufficient system could release cofactor (NADP<SUP>+</SUP>) and cosubstrate (<SMALL>L</SMALL>-Glutamine) regenerated simultaneously. The recombinant <I>E. coli</I> BL21 (SGMP) with cofactor self-sufficient whole-cell cascade biocatalysis showed high ee value (>99%) and high yield, with 99.6% conversion of epoxide (<I>S</I>)-<B>1a</B> to 1,2-amino alcohol (<I>S</I>)-<B>1d</B> in 10 h. It further converted (<I>S</I>)-<B>2a</B>-<B>5a</B> to (<I>S</I>)-<B>2d</B>-<B>5d</B> with varying conversion rates ranging between 65-96.4%. This study first provides one-step synthesis of optically pure 1,2-amino alcohols from (<I>S</I>)-epoxides employing a synthetic redox-self-sufficient cascade.</P><BR>[FIG OMISSION]</BR>

발행연도

2019

발행기관

American Chemical Society

ISSN

2161-5063

8

4

페이지

pp.734-743

주제어

1,2-amino alcohols; epoxides; ω-transaminase; self-sufficient; whole-cell biocatalyst

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1 2023-12-11

논문; 2019-12-31

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