Dimeric β-cyclodextrin-based supramolecular ligands and their copper(II) complexes as metalloenzyme models

Won Bae Jeon; Kwang Hee Bae; Si Myung Byun

doi:10.1016/S0162-0134(98)10049-1

Dimeric β-cyclodextrin-based supramolecular ligands and their copper(II) complexes as metalloenzyme models

Won Bae Jeon, Kwang Hee Bae, Si Myung Byun

Division of Biotechnology

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

12 Scopus citations

Abstract

New supramolecular ligands possessing linear 13- and 15-membered pyridine diamidetriamine chelators between the primary sides of two β- cyclodextrin cavities were synthesized, and characterized by MALDI-MS, NMR, IR and UV-Visible spectroscopy. Fluorescence and pH-metric titration were carried out in order to ascertain their behavior as bifunctional hosts for fluorescent guests and Cu(II) ion. The pK(a) value for the Cu(II) promoted deprotonation of amide ligands was determined to be 6.2 from pH-absorbance profile. Above pH 8.0, two deprotonated amides and three amino groups chelated Cu(II) ion, and yielded penta-coordinated Cu(II) complexes. The Cu(II) complexes catalyzed the hydrolysis of p-nitrophenyl acetate, adamantate and amino acids. Especially, the complex containing 13-membered chelator is an artificial metalloesterase with catalytic rate constant k(cat)=3.8 x 10^-3 min^-1 and Michaelis constant K(m)=3.5 x 10^-4 M for the hydrolysis of p-nitrophenyl adamantate via metal-hydroxide mechanism.

Original language	English
Pages (from-to)	163-169
Number of pages	7
Journal	Journal of Inorganic Biochemistry
Volume	71
Issue number	3-4
DOIs	https://doi.org/10.1016/S0162-0134(98)10049-1
State	Published - Sep 1998

Bibliographical note

Funding Information:
This work was supported by a grant from the Korea Science and Engineering Foundation, and the Research Center for New Bio-Materials in Agriculture (SRC) in part.

Keywords

Copper(II) complex
Metal-hydroxide mechanism
Metalloenzyme model
β-Cyclodextrin

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10.1016/S0162-0134(98)10049-1

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@article{672fa5cce2594745ae93c39e51ed2a75,

title = "Dimeric β-cyclodextrin-based supramolecular ligands and their copper(II) complexes as metalloenzyme models",

abstract = "New supramolecular ligands possessing linear 13- and 15-membered pyridine diamidetriamine chelators between the primary sides of two β- cyclodextrin cavities were synthesized, and characterized by MALDI-MS, NMR, IR and UV-Visible spectroscopy. Fluorescence and pH-metric titration were carried out in order to ascertain their behavior as bifunctional hosts for fluorescent guests and Cu(II) ion. The pK(a) value for the Cu(II) promoted deprotonation of amide ligands was determined to be 6.2 from pH-absorbance profile. Above pH 8.0, two deprotonated amides and three amino groups chelated Cu(II) ion, and yielded penta-coordinated Cu(II) complexes. The Cu(II) complexes catalyzed the hydrolysis of p-nitrophenyl acetate, adamantate and amino acids. Especially, the complex containing 13-membered chelator is an artificial metalloesterase with catalytic rate constant k(cat)=3.8 x 10-3 min-1 and Michaelis constant K(m)=3.5 x 10-4 M for the hydrolysis of p-nitrophenyl adamantate via metal-hydroxide mechanism.",

keywords = "Copper(II) complex, Metal-hydroxide mechanism, Metalloenzyme model, β-Cyclodextrin",

author = "Jeon, \{Won Bae\} and Bae, \{Kwang Hee\} and Byun, \{Si Myung\}",

note = "Funding Information: This work was supported by a grant from the Korea Science and Engineering Foundation, and the Research Center for New Bio-Materials in Agriculture (SRC) in part.",

year = "1998",

month = sep,

doi = "10.1016/S0162-0134(98)10049-1",

language = "English",

volume = "71",

pages = "163--169",

journal = "Journal of Inorganic Biochemistry",

issn = "0162-0134",

publisher = "Elsevier Inc.",

number = "3-4",

}

TY - JOUR

T1 - Dimeric β-cyclodextrin-based supramolecular ligands and their copper(II) complexes as metalloenzyme models

AU - Jeon, Won Bae

AU - Bae, Kwang Hee

AU - Byun, Si Myung

N1 - Funding Information: This work was supported by a grant from the Korea Science and Engineering Foundation, and the Research Center for New Bio-Materials in Agriculture (SRC) in part.

PY - 1998/9

Y1 - 1998/9

N2 - New supramolecular ligands possessing linear 13- and 15-membered pyridine diamidetriamine chelators between the primary sides of two β- cyclodextrin cavities were synthesized, and characterized by MALDI-MS, NMR, IR and UV-Visible spectroscopy. Fluorescence and pH-metric titration were carried out in order to ascertain their behavior as bifunctional hosts for fluorescent guests and Cu(II) ion. The pK(a) value for the Cu(II) promoted deprotonation of amide ligands was determined to be 6.2 from pH-absorbance profile. Above pH 8.0, two deprotonated amides and three amino groups chelated Cu(II) ion, and yielded penta-coordinated Cu(II) complexes. The Cu(II) complexes catalyzed the hydrolysis of p-nitrophenyl acetate, adamantate and amino acids. Especially, the complex containing 13-membered chelator is an artificial metalloesterase with catalytic rate constant k(cat)=3.8 x 10-3 min-1 and Michaelis constant K(m)=3.5 x 10-4 M for the hydrolysis of p-nitrophenyl adamantate via metal-hydroxide mechanism.

AB - New supramolecular ligands possessing linear 13- and 15-membered pyridine diamidetriamine chelators between the primary sides of two β- cyclodextrin cavities were synthesized, and characterized by MALDI-MS, NMR, IR and UV-Visible spectroscopy. Fluorescence and pH-metric titration were carried out in order to ascertain their behavior as bifunctional hosts for fluorescent guests and Cu(II) ion. The pK(a) value for the Cu(II) promoted deprotonation of amide ligands was determined to be 6.2 from pH-absorbance profile. Above pH 8.0, two deprotonated amides and three amino groups chelated Cu(II) ion, and yielded penta-coordinated Cu(II) complexes. The Cu(II) complexes catalyzed the hydrolysis of p-nitrophenyl acetate, adamantate and amino acids. Especially, the complex containing 13-membered chelator is an artificial metalloesterase with catalytic rate constant k(cat)=3.8 x 10-3 min-1 and Michaelis constant K(m)=3.5 x 10-4 M for the hydrolysis of p-nitrophenyl adamantate via metal-hydroxide mechanism.

KW - Copper(II) complex

KW - Metal-hydroxide mechanism

KW - Metalloenzyme model

KW - β-Cyclodextrin

UR - https://www.scopus.com/pages/publications/0344541825

U2 - 10.1016/S0162-0134(98)10049-1

DO - 10.1016/S0162-0134(98)10049-1

M3 - Article

C2 - 9833322

AN - SCOPUS:0344541825

SN - 0162-0134

VL - 71

SP - 163

EP - 169

JO - Journal of Inorganic Biochemistry

JF - Journal of Inorganic Biochemistry

IS - 3-4

ER -

Dimeric β-cyclodextrin-based supramolecular ligands and their copper(II) complexes as metalloenzyme models

Abstract

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Keywords

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