Cyclodextrin-based artificial oxidases with high rate accelerations and selectivity

You Zhou; Emil Anders Lindbäck; Christian Marcus Pedersen; Mikael Bols

doi:10.1016/j.tetlet.2014.02.100

Cyclodextrin-based artificial oxidases with high rate accelerations and selectivity

You Zhou, Emil Anders Lindbäck, Christian Marcus Pedersen, Mikael Bols^*

^*Corresponding author for this work

Department of Chemistry

9 Citations (Scopus)

Abstract

Three cyclodextrin derivatives with one to four 2-O-formylmethyl groups attached to the secondary rim were prepared and investigated as catalysts for the oxidation of aminophenols in buffered dilute hydrogen peroxide. The derivatives were found to be Michaelis-Menten catalysts and to give rate accelerations of up to 20,000 for the oxidation of 2-aminophenol to 2-amino-phenoxazin-3-one, and 12,000 for the oxidation of 2-amino-p-cresol to 2-nitro-p-cresol. While a range of differently substituted substrates was oxidized the success of the reaction was highly dependent on the substituent pattern. The ability of one of the new artificial enzymes to oxidize selectively one aminophenol from a mixture of two was investigated giving substrate selectivities of up to 16:1.

Original language	English
Journal	Tetrahedron Letters
Volume	55
Issue number	14
Pages (from-to)	2304-2307
Number of pages	4
ISSN	0040-4039
DOIs	https://doi.org/10.1016/j.tetlet.2014.02.100
Publication status	Published - 2014

Keywords

Catalysis
Chemzymes
Hydrogen peroxide
Michaelis-Menten
Peroxidase

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10.1016/j.tetlet.2014.02.100

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title = "Cyclodextrin-based artificial oxidases with high rate accelerations and selectivity",

abstract = "Three cyclodextrin derivatives with one to four 2-O-formylmethyl groups attached to the secondary rim were prepared and investigated as catalysts for the oxidation of aminophenols in buffered dilute hydrogen peroxide. The derivatives were found to be Michaelis-Menten catalysts and to give rate accelerations of up to 20,000 for the oxidation of 2-aminophenol to 2-amino-phenoxazin-3-one, and 12,000 for the oxidation of 2-amino-p-cresol to 2-nitro-p-cresol. While a range of differently substituted substrates was oxidized the success of the reaction was highly dependent on the substituent pattern. The ability of one of the new artificial enzymes to oxidize selectively one aminophenol from a mixture of two was investigated giving substrate selectivities of up to 16:1.",

keywords = "Catalysis, Chemzymes, Hydrogen peroxide, Michaelis-Menten, Peroxidase",

author = "You Zhou and Lindb{\"a}ck, {Emil Anders} and Pedersen, {Christian Marcus} and Mikael Bols",

year = "2014",

doi = "10.1016/j.tetlet.2014.02.100",

language = "English",

volume = "55",

pages = "2304--2307",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Pergamon Press",

number = "14",

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TY - JOUR

T1 - Cyclodextrin-based artificial oxidases with high rate accelerations and selectivity

AU - Zhou, You

AU - Lindbäck, Emil Anders

AU - Pedersen, Christian Marcus

AU - Bols, Mikael

PY - 2014

Y1 - 2014

N2 - Three cyclodextrin derivatives with one to four 2-O-formylmethyl groups attached to the secondary rim were prepared and investigated as catalysts for the oxidation of aminophenols in buffered dilute hydrogen peroxide. The derivatives were found to be Michaelis-Menten catalysts and to give rate accelerations of up to 20,000 for the oxidation of 2-aminophenol to 2-amino-phenoxazin-3-one, and 12,000 for the oxidation of 2-amino-p-cresol to 2-nitro-p-cresol. While a range of differently substituted substrates was oxidized the success of the reaction was highly dependent on the substituent pattern. The ability of one of the new artificial enzymes to oxidize selectively one aminophenol from a mixture of two was investigated giving substrate selectivities of up to 16:1.

AB - Three cyclodextrin derivatives with one to four 2-O-formylmethyl groups attached to the secondary rim were prepared and investigated as catalysts for the oxidation of aminophenols in buffered dilute hydrogen peroxide. The derivatives were found to be Michaelis-Menten catalysts and to give rate accelerations of up to 20,000 for the oxidation of 2-aminophenol to 2-amino-phenoxazin-3-one, and 12,000 for the oxidation of 2-amino-p-cresol to 2-nitro-p-cresol. While a range of differently substituted substrates was oxidized the success of the reaction was highly dependent on the substituent pattern. The ability of one of the new artificial enzymes to oxidize selectively one aminophenol from a mixture of two was investigated giving substrate selectivities of up to 16:1.

KW - Catalysis

KW - Chemzymes

KW - Hydrogen peroxide

KW - Michaelis-Menten

KW - Peroxidase

U2 - 10.1016/j.tetlet.2014.02.100

DO - 10.1016/j.tetlet.2014.02.100

M3 - Journal article

AN - SCOPUS:84897379148

SN - 0040-4039

VL - 55

SP - 2304

EP - 2307

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 14

ER -

Cyclodextrin-based artificial oxidases with high rate accelerations and selectivity

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Keywords

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