Binding geometry, stoichiometry, and thermodynamics of cyclomalto-oligosaccharide (cyclodextrin) inclusion complex formation with chlorogenic acid, the major substrate of apple polyphenol oxidase

Irwin, Peter L.; Pfeffer, Philip E.; Doner, Landis W.; Sapers, G. M.; Brewster, Jeffrey D.; Nagahashi, Gerald; Hicks, Kevin B.

doi:10.1016/0008-6215(94)84223-x

Cited by 57 publications

(38 citation statements)

References 19 publications

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“…[29][30][31][32] However, individual protons will shift to varying extents, depending on the nature of the environment they are in and the proximity of anisotropy-producing functional groups. The nonspecific solvent effect of (SBE) 7m -␤-CD or HP-␤-CD on the chemical shifts of various protons is not likely to be a significant factor at the cyclodextrin concentrations used here.…”

Section: Nmr Studiesmentioning

confidence: 99%

Comparative Effects of (SBE)7m‐β‐CD and HP‐β‐CD on the Stability of Two Anti‐neoplastic Agents, Melphalan and Carmustine

Quintanar‐Guerrero

Rajewski²,

Velde

et al. 2000

Journal of Pharmaceutical Sciences

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Section: Nmr Studiesmentioning

confidence: 99%

Comparative Effects of (SBE)7m‐β‐CD and HP‐β‐CD on the Stability of Two Anti‐neoplastic Agents, Melphalan and Carmustine

Quintanar‐Guerrero

Rajewski²,

Velde

et al. 2000

Journal of Pharmaceutical Sciences

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“…The utility of these materials was recognized for many applications: they were used for synthetic purposes [167,168] (catalysis...), in thermochemistry [181], food [120,171,175], and pharmaceutical [161] industries, and in other fields such as the clean-up of industrial waste effluents [18,185,186] and in chromatography (separation of molecules...) [145,148,160]. More specifically, polymerized CD gels are preferentially used as stationary phases in column chromatography for gel inclusion chromatography with some degree of success.…”

Section: Cyclodextrin Polymers and Copolymersmentioning

confidence: 99%

Synthesis and applications of adsorbents containing cyclodextrins

Crini¹,

2002

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Synthesis and applications of adsorbents containing cyclodextrinsCyclodextrins (CDs), which possess a hydrophobic cavity, have a remarkable capacity to form inclusion complexes with various molecules through host-guest interactions. It is well known that the usefulness of CDs is due to the combination of the inclusion properties and structural features of these molecules. CDs are used extensively in separation science because CD-complexation phenomena offer a procedure of choice for separation of compounds and extraction processes, and provide a useful and versatile tool for protecting the environment. The present review shows the advantages accruing from the use of adsorbents containing cyclodextrins, in particular in chromatographic separations and in waste water treatment. The main goal of this review is to provide a summary of the information concerning the synthesis of materials containing CDs and to give a general overview of the different possible applications of CDs as sorbents in the field of separation techniques. Recent and continuing interest in these adsorbents is evident from the number of papers that appear each year in the literature.

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“…These studies, mainly using NMR spectroscopy and UV spectrophotometry, showed that the dissociation constants of the phenol-CD complex (assuming a 1:1 stoichiometry) widely varied according to the nature of the phenol and of the CD. In the latter study, the authors concluded that the enzymatic browning control was mainly due to the sequestration of PPO substrates by CD (35).…”

mentioning

confidence: 95%

Effect of Cyclodextrins on Polyphenol Oxidation Catalyzed by Apple Polyphenol Oxidase

Billaud

Regaudie

Fayad

et al. 1995

ACS Symposium Series

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In order to find nonsulfite antibrowning agents for the food industry, cyclodextrins (CD) have been tested. CD are able to form inclusion compounds with polyphenols and inhibition properties have been studied in model solutions containing one or two phenols and purified apple polyphenol oxidase (PPO). The dissociation constants (K D ) of a series of phenolic compounds with α-CD, β-CD and hydroxypropyl-β-CD have been determined both by enzymatic kinetic analysis and NMR experiments in solution with one phenol. Large differences have been found among the phenols tested resulting in wide variations in the inhibitory properties of CD. In the mixtures of two phenolic compounds, addition of β-CD can result either in a large inhibition, a slight inhibition, or even a slight activation of oxygen uptake, depending on the kinetic constants and of the phenols present in the solution. Moreover, since β-CD induced a modification of the balance of free substrates in a multiphenolic solution, the colors obtained after enzymatic oxidation catalyzed by PPO can also be modified in different ways by addition of β-CD as demonstrated on the 3 types of mixtures of two phenolic compounds that we have tested, namely chlorogenic acid / (-)-epicatechin, chlorogenic acid / (+)-catechin and 4-methylcatechol / caffeic acid.Enzymatic browning which occurs during handling, storage and processing of fruits and vegetables is mainly initiated by the enzyme polyphenol oxidase (odiphenol : oxygen oxidoreductase EC 1.10.3.1) or PPO (7, 2). The loss of cell integrity results in the decompartmentation of phenolic substrates and enzymes and then, in the presence of molecular oxygen, the oxidative production of colored quinones (3). Brown pigmentation following this enzymatic reaction and subsequent non enzymatic 0097^156/95/0600-0295$12.00/0

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Binding geometry, stoichiometry, and thermodynamics of cyclomalto-oligosaccharide (cyclodextrin) inclusion complex formation with chlorogenic acid, the major substrate of apple polyphenol oxidase

Cited by 57 publications

References 19 publications

Comparative Effects of (SBE)7m‐β‐CD and HP‐β‐CD on the Stability of Two Anti‐neoplastic Agents, Melphalan and Carmustine

Comparative Effects of (SBE)7m‐β‐CD and HP‐β‐CD on the Stability of Two Anti‐neoplastic Agents, Melphalan and Carmustine

Synthesis and applications of adsorbents containing cyclodextrins

Effect of Cyclodextrins on Polyphenol Oxidation Catalyzed by Apple Polyphenol Oxidase

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