Nonenzymatic and metal-free organocatalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen

Chenjie Zhu; Qing Li; Lingling Pu; Zhuotao Tan; Kai Guo; Hanjie Ying; Pingkai Ouyang

doi:10.1021/acscatal.6b01261

Nonenzymatic and metal-free organocatalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen

Chenjie Zhu, Qing Li, Lingling Pu, Zhuotao Tan, Kai Guo, Hanjie Ying, Pingkai Ouyang

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

Abstract

The application of synthetic flavinium organocatalysts for the in situ regeneration of oxidized cofactors NAD(P)⁺ using O₂ as the terminal oxidant without any special illumination or equipment is reported. With the aid of the highly active bridged flavinium catalyst, the rate of NAD(P)H oxidation is accelerated by 3 orders of magnitude. The results show that the catalytic activity of the bridged flavinium catalyst is not dependent on light but on only oxygen. Furthermore, this catalyst is compatible with various preparative enzymatic oxidation reactions. A hydride transfer mechanism is proposed for the presented system.

Original language	English
Pages (from-to)	4989-4994
Number of pages	6
Journal	ACS Catalysis
Volume	6
Issue number	8
DOIs	https://doi.org/10.1021/acscatal.6b01261
State	Published - 5 Aug 2016

Keywords

aerobic oxidation
cofactor regeneration
enzyme catalysis
flavin
metal-free catalysis
organocatalysis

Access to Document

10.1021/acscatal.6b01261

Cite this

@article{78b56b094c424a1aacd7686e6fcb7a9a,

title = "Nonenzymatic and metal-free organocatalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen",

abstract = "The application of synthetic flavinium organocatalysts for the in situ regeneration of oxidized cofactors NAD(P)+ using O2 as the terminal oxidant without any special illumination or equipment is reported. With the aid of the highly active bridged flavinium catalyst, the rate of NAD(P)H oxidation is accelerated by 3 orders of magnitude. The results show that the catalytic activity of the bridged flavinium catalyst is not dependent on light but on only oxygen. Furthermore, this catalyst is compatible with various preparative enzymatic oxidation reactions. A hydride transfer mechanism is proposed for the presented system.",

keywords = "aerobic oxidation, cofactor regeneration, enzyme catalysis, flavin, metal-free catalysis, organocatalysis",

author = "Chenjie Zhu and Qing Li and Lingling Pu and Zhuotao Tan and Kai Guo and Hanjie Ying and Pingkai Ouyang",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = aug,

day = "5",

doi = "10.1021/acscatal.6b01261",

language = "英语",

volume = "6",

pages = "4989--4994",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Nonenzymatic and metal-free organocatalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen

AU - Zhu, Chenjie

AU - Li, Qing

AU - Pu, Lingling

AU - Tan, Zhuotao

AU - Guo, Kai

AU - Ying, Hanjie

AU - Ouyang, Pingkai

PY - 2016/8/5

Y1 - 2016/8/5

N2 - The application of synthetic flavinium organocatalysts for the in situ regeneration of oxidized cofactors NAD(P)+ using O2 as the terminal oxidant without any special illumination or equipment is reported. With the aid of the highly active bridged flavinium catalyst, the rate of NAD(P)H oxidation is accelerated by 3 orders of magnitude. The results show that the catalytic activity of the bridged flavinium catalyst is not dependent on light but on only oxygen. Furthermore, this catalyst is compatible with various preparative enzymatic oxidation reactions. A hydride transfer mechanism is proposed for the presented system.

AB - The application of synthetic flavinium organocatalysts for the in situ regeneration of oxidized cofactors NAD(P)+ using O2 as the terminal oxidant without any special illumination or equipment is reported. With the aid of the highly active bridged flavinium catalyst, the rate of NAD(P)H oxidation is accelerated by 3 orders of magnitude. The results show that the catalytic activity of the bridged flavinium catalyst is not dependent on light but on only oxygen. Furthermore, this catalyst is compatible with various preparative enzymatic oxidation reactions. A hydride transfer mechanism is proposed for the presented system.

KW - aerobic oxidation

KW - cofactor regeneration

KW - enzyme catalysis

KW - flavin

KW - metal-free catalysis

KW - organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=84981320433&partnerID=8YFLogxK

U2 - 10.1021/acscatal.6b01261

DO - 10.1021/acscatal.6b01261

M3 - 文章

AN - SCOPUS:84981320433

SN - 2155-5435

VL - 6

SP - 4989

EP - 4994

JO - ACS Catalysis

JF - ACS Catalysis

IS - 8

ER -

Nonenzymatic and metal-free organocatalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this