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Upgraded bioelectrocatalytic N2 fixation: From N2 to chiral amine intermediates

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논문

Upgraded bioelectrocatalytic N2 fixation: From N2 to chiral amine intermediates

학술지

Journal of the American Chemical Society

저자명

Chen, Hui; Cai, Rong; Patel, Janki; Dong, Fangyuan; Chen, Hsiaonung; Minteer, Shelley D.

초록

<P>Enantiomerically pure chiral amines are of increasing value in the preparation of bioactive compounds, pharmaceuticals, and agrochemicals. &omega;-Transaminase (&omega;-TA) is an ideal catalyst for asymmetric amination because of its excellent enantioselectivity and wide substrate scope. To shift the equilibrium of reactions catalyzed by &omega;-TA to the side of the amine product, an upgraded N<SUB>2</SUB> fixation system based on bioelectrocatalysis was developed to realize the conversion from N<SUB>2</SUB> to chiral amine intermediates. The produced NH<SUB>3</SUB> was in situ reacted with <SMALL>L</SMALL>-alanine dehydrogenase to generate alanine with NADH as a coenzyme. &omega;-TA transferred the amino group from alanine to ketone substrates and finally produced the desired chiral amine intermediates. The cathode of the upgraded N<SUB>2</SUB> fixation system supplied enough reducing power to synchronously realize the regeneration of reduced methyl viologen (MV<SUP>&#x2022;+</SUP>) and NADH for the nitrogenase and <SMALL>L</SMALL>-alanine dehydrogenase. The coproduct, pyruvate, was consumed by <SMALL>L</SMALL>-alanine dehydrogenase to regenerate alanine and push the equilibrium to the side of amine. After 10 h of reaction, the concentration of 1-methyl-3-phenylpropylamine achieved 0.54 mM with the 27.6% highest faradaic efficiency and >99% enantiomeric excess (ee<SUB>p</SUB>). Because of the wide substrate scope and excellent enantioselectivity of &omega;-TA, the upgraded N<SUB>2</SUB> fixation system has great potential to produce a variety of chiral amine intermediates for pharmaceuticals and other applications.</P><BR>[FIG OMISSION]</BR>

발행연도

2019

발행기관

American Chemical Society

라이선스

cc-by-nc

ISSN

0002-7863

ISSN

1520-5126

141

12

페이지

pp.4963-4971

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1 2023-12-11
2 2023-12-11

논문; 2019-12-31

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