Preparation and Characterization of the Solid Inclusion Compounds of α-, β-Cyclodextrin with Phenylalanine (D-, L- and DL-Phe) and Tryptophan (D-, L- and DL-Trp)

Song, Le Xin; Teng, Chuan Feng; Yang, Yongying

doi:10.1007/s10847-005-7970-8

Cited by 39 publications

(24 citation statements)

References 35 publications

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“…(a) that between the amino group of L‐Phe and glycosidic bonds of β‐CD, hydrogen bonds (2.023 Å) are formed, which was in agreement with the findings of Song et al . (), who suggested that aromatic ring of a guest molecule within a host cavity might be kept near small end side of cavity. The cluster analyses of the docking runs of L‐Phe with β‐CD is shown in Supplementary data (Fig.…”

Section: Resultsmentioning

confidence: 99%

The role of pulsed electric fields treatment in enhancing the stability of amino acid – sugar complexes:‐ interactions between L‐Phenylalanine and β‐Cyclodextrin

Wang

Zeng

Brennan

et al. 2016

Int J of Food Sci Tech

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In this work, the effect of pulsed electric fields (PEF) treatment on the interactions between amino acids (using L-Phenylalanine: L-Phe) and sugar (using b-Cyclodextrin: b-CD) complex was analysed by fluorescence spectroscopy, Raman spectroscopy and simultaneous thermal analyzer. Moreover, the molecular dynamics of b-CD-L-Phe inclusion complex treated by PEF was calculated by molecular modelling. The results indicated that b-CD-L-Phe complexes are formed by a molar ratio of 1:1, and the stability constant of such complexes increased from 147 to 614 M À1 by PEF treatment. Thermal characterisations of b-CD-L-Phe complexes indicated that the PEF treatment could increase the yield of complexes. The PEF treatment resulted in an increase in the reaction enthalpy of b-CD-L-Phe inclusion complexes by DSC curve. These results show that PEF treatment has the potential to promote the chemical processing, especially the small organic molecules participate in inclusion or cross-linking reaction.

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Section: Resultsmentioning

confidence: 99%

The role of pulsed electric fields treatment in enhancing the stability of amino acid – sugar complexes:‐ interactions between L‐Phenylalanine and β‐Cyclodextrin

Wang

Zeng

Brennan

et al. 2016

Int J of Food Sci Tech

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“…It should be remembered that the thermodynamics parameters for the amino acids complexes with CDs strongly depend on the pH of a solution [27,28]. From available experimental data for the Phe-CD complexes we chose the ones which were recorded at pH as close as possible to the current investigations.…”

Section: Theoretical Calculationsmentioning

confidence: 99%

Enhanced enzymatic activity of phenylalanine dehydrogenase caused by cyclodextrins

Gubica

Pałka

Szeleszczuk

et al. 2015

Journal of Molecular Catalysis B: Enzymatic

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“…1 H-and 13 C-NMR spectra of free a-CD, Syr and their inclusion complex in D 2 O were recorded at 298.2 K using a Bruker NMR spectrometer operating at 300 and 75 MHz, respectively. 2,2-Dimethyl-2-silapentane-5-sulfonate sodium salt (DSS) was used as internal reference in all cases.…”

Section: ϫ3mentioning

confidence: 99%

“…Many papers have been published concerning the formation and spectral properties of guest-CD complexes in aqueous solution using various analytical methods. [2][3][4][5][6] In solution, phenol and its simple analogs can be partly or wholly included into a CD cavity. 7) There have been a few structural studies on the inclusion complexes of CDs with phenol and substituted phenols based on experimental measurements or theoretical calculations.…”

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confidence: 99%

Experimental and Theoretical Studies on the Inclusion Complexation of Syringic Acid with .ALPHA.-, .BETA.-, .GAMMA.- and Heptakis(2,6-di-O-methyl)-.BETA.-cyclodextrin

Song

Wang

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Cyclodextrins (CDs, Fig. 1) are cyclic oligosaccharides consisting of glucose subunits connected through glycosidic a-1,4 bond, forming a structure as a hollow truncate with one ring wider than the other.1) The most common CDs are a-, b-and g-CD, composed of six, seven and eight glucose units, respectively. Heptakis(2,6-di-O-methyl)-b-CD (DMb-CD) is a simple derivative of b-CD, in which all 2-and 6-OH groups of the seven glucose units are substituted by -OCH 3 groups. Many papers have been published concerning the formation and spectral properties of guest-CD complexes in aqueous solution using various analytical methods. [2][3][4][5][6] In solution, phenol and its simple analogs can be partly or wholly included into a CD cavity. 7) There have been a few structural studies on the inclusion complexes of CDs with phenol and substituted phenols based on experimental measurements or theoretical calculations. [8][9][10][11] Huang and his coworkers performed a detailed investigation on the conformation and stabilization energies of CD inclusion complexes of several substituted phenols, including 2-methylphenol, 2-ethylphenol and 2-isopropylphenol, using semiempirical molecular orbital method. 8) These authors pointed out that one of the principal driving forces for the formation of the inclusion complexes should be attributed to van der Waals interaction.Previous experimental studies showed that there were no enough strong interactions between a parent CD and phenol or its simple derivatives such as nitrophenol, methylphenol, aminophenol, halogenphenol and hydroxydiphenyl.12-14) However, it is found that eugenol (Eug), a phenol derivative with three substituents on benzene ring, while being accommodated into CD cavity, is able to form considerably stable inclusion complexes with three common parent CDs. 9) These results urge us to estimate the effects of the number of substituted groups (NSG) in guest and the molar volume ratio (MVR) of guest to the cavity of CD on the formation and stability of CD supramolecular complexes of phenol derivatives.Syringic acid (Syr) is usually used as sedative and local anaesthetic. 2-Methoxylphenol (2-Mop), with antitussive and expectorant effects, is widely used as a medicine for bronchitis. Eugenol is known to be an effective snake repellent. The three molecules are the important derivatives of phenol. Their structure features and molar volumes are displayed in Fig. 2.CDs are known to form inclusion complexes with a variety of organic guests.3,6) Introduction of CD into the pharmaceutical process can alter the solubility and stability of included medicines so as to be applied as drug carriers in some chemotherapy. In the present work, a-, b-and g-CD are selected as hosts to assess the influence of different sizes of CD cavities on the stability of the CD supramolecular complexes of Syr. In addition, in order to estimate the effects of NSG and MVR on the binding abilities of CDs in aqueous solution, a a-, b b-, g g-and heptakis(2,6-di-O-methyl)

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Preparation and Characterization of the Solid Inclusion Compounds of α-, β-Cyclodextrin with Phenylalanine (D-, L- and DL-Phe) and Tryptophan (D-, L- and DL-Trp)

Cited by 39 publications

References 35 publications

The role of pulsed electric fields treatment in enhancing the stability of amino acid – sugar complexes:‐ interactions between L‐Phenylalanine and β‐Cyclodextrin

The role of pulsed electric fields treatment in enhancing the stability of amino acid – sugar complexes:‐ interactions between L‐Phenylalanine and β‐Cyclodextrin

Enhanced enzymatic activity of phenylalanine dehydrogenase caused by cyclodextrins

Experimental and Theoretical Studies on the Inclusion Complexation of Syringic Acid with .ALPHA.-, .BETA.-, .GAMMA.- and Heptakis(2,6-di-O-methyl)-.BETA.-cyclodextrin

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