WANG Bing, HU Zhiwen, ZHENG Hailing, et al. Oxidation of catechol catalyzed by β-cyclodextrin-Cu(Ⅱ) complexes and its reaction kinetics[J]. CIESC Journal, 2009, (6): 1459-1465.
WANG Bing, HU Zhiwen, ZHENG Hailing, et al. Oxidation of catechol catalyzed by β-cyclodextrin-Cu(Ⅱ) complexes and its reaction kinetics[J]. CIESC Journal, 2009, (6): 1459-1465.DOI:
Two kinds of β-cyclodextrin (β-CD) derivatives mono-6-(N-histamino)-6-deoxy-β-cyclodextrin (6-His-β-CD) and mono-2-(N-histamino)-2-deoxy-β-cyclodextrin (2-His-β-CD) were prepared by reacting β-CD withp-toluene sulfonyl chloride
displacement the monotosylate with iodide
and finally the reaction of cyclodextrin iodide with nucleophile L-histidine.From these derivatives
the β-CD-Cu(Ⅱ) complexes (Cu(Ⅱ)/6-His-β-CD, Cu(Ⅱ)/2-His-β-CD) with polyphenol oxidase (PPO) activity were synthesized.The derivatives and the complexes were characterized with elemental analysis
Fourier-transform infrared spectroscopy
nuclear magnetic resonance spectroscopy and atomic absorption spectrometry.The complexes were used as catalysts for the oxidation of catechol using O2 as the oxidant
which was monitored by UV-Vis spectrophotometer.The effects of temperature and pH value on the reaction were also studied.The results indicated that the PPO mimics exhibited high catalytic activities.Cu(Ⅱ)/2-His-β-CD showed higher PPO activity than Cu(Ⅱ)/6-His-β-CD.The kinetic studies showed that all three factors
the hydrophobic environment provided by β-CD
the Cu(Ⅱ) bound to the histamine and the base catalysis contributed to the PPO activity.