Preprint Article Version 1 This version is not peer-reviewed

Catalysis of Henry Reaction by Plasmid DNA

Version 1 : Received: 9 November 2018 / Approved: 13 November 2018 / Online: 13 November 2018 (11:26:56 CET)

How to cite: Di, X.; Zhang, X.; Wang, Y.; Wang, Y.; Lai, C.; Wu, X.; Liu, P.; Liu, S.; Gao, R. Catalysis of Henry Reaction by Plasmid DNA. Preprints 2018, 2018110313 (doi: 10.20944/preprints201811.0313.v1). Di, X.; Zhang, X.; Wang, Y.; Wang, Y.; Lai, C.; Wu, X.; Liu, P.; Liu, S.; Gao, R. Catalysis of Henry Reaction by Plasmid DNA. Preprints 2018, 2018110313 (doi: 10.20944/preprints201811.0313.v1).

Abstract

This work demonstrates that a plasmid can function as an efficient biocatalyst in mediating the nitroaldol (Henry) reaction at high temperatures in ultrapure water. Compared with ssDNA, the plasmid displayed a remarkable catalytic efficiency (97% yield within 20 min). Aromatic aldehydes which bear strong or moderate electron-withdrawing groups reacted satisfactorily with nitromethane, which afforded the corresponding β-nitroalcohols in good yields within 2 h (up to 98%). By contrast, aliphatic and aromatic aldehydes with electron-donating groups did not react. Moreover, the yield significantly dropped when the size of the carbanion increased, and the yield was only 10% when nitropropane was used as the donor.

Subject Areas

ssDNA; plasmid; pcDNA3.1; Henry Reaction; C-C bond formation

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