Artificial enzymes based on cyclodextrin with phenol as the catalytic group

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

doi:10.1016/j.tetlet.2012.07.050

Artificial enzymes based on cyclodextrin with phenol as the catalytic group

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

Department of Chemistry

9 Citations (Scopus)

Abstract

β-Cyclodextrin containing one or two N-linked ortho-N- acetylaminophenols has been synthesized and tested for their properties as artificial glycosidases. Four different para-nitrophenyl glycosides were used as substrates and k _cat/k _uncat values of up to 381 were found for the di-functionalized products, whereas the mono derivative showed up to 47 times rate enhancement. The optimum pH for the catalysis was found to be approximately pH 8 and the influence of phosphate concentration was investigated.

Original language	English
Journal	Tetrahedron Letters
Volume	53
Issue number	37
Pages (from-to)	5023-5026
Number of pages	4
ISSN	0040-4039
DOIs	https://doi.org/10.1016/j.tetlet.2012.07.050
Publication status	Published - 12 Sept 2012

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title = "Artificial enzymes based on cyclodextrin with phenol as the catalytic group",

abstract = "β-Cyclodextrin containing one or two N-linked ortho-N- acetylaminophenols has been synthesized and tested for their properties as artificial glycosidases. Four different para-nitrophenyl glycosides were used as substrates and k cat/k uncat values of up to 381 were found for the di-functionalized products, whereas the mono derivative showed up to 47 times rate enhancement. The optimum pH for the catalysis was found to be approximately pH 8 and the influence of phosphate concentration was investigated.",

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

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AU - Lindbäck, Emil Anders

AU - Zhou, You

AU - Pedersen, Christian Marcus

AU - Bols, Mikael

PY - 2012/9/12

Y1 - 2012/9/12

N2 - β-Cyclodextrin containing one or two N-linked ortho-N- acetylaminophenols has been synthesized and tested for their properties as artificial glycosidases. Four different para-nitrophenyl glycosides were used as substrates and k cat/k uncat values of up to 381 were found for the di-functionalized products, whereas the mono derivative showed up to 47 times rate enhancement. The optimum pH for the catalysis was found to be approximately pH 8 and the influence of phosphate concentration was investigated.

AB - β-Cyclodextrin containing one or two N-linked ortho-N- acetylaminophenols has been synthesized and tested for their properties as artificial glycosidases. Four different para-nitrophenyl glycosides were used as substrates and k cat/k uncat values of up to 381 were found for the di-functionalized products, whereas the mono derivative showed up to 47 times rate enhancement. The optimum pH for the catalysis was found to be approximately pH 8 and the influence of phosphate concentration was investigated.

U2 - 10.1016/j.tetlet.2012.07.050

DO - 10.1016/j.tetlet.2012.07.050

M3 - Journal article

SN - 0040-4039

VL - 53

SP - 5023

EP - 5026

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Artificial enzymes based on cyclodextrin with phenol as the catalytic group

Abstract

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