Molecular Recognition Study on Supramolecular Systems. 20. Molecular Recognition and Enantioselectivity of Aliphatic Alcohols by <scp>l</scp>-Tryptophan-Modified β-Cyclodextrin

Liu, Yu; Han, Bao‐Hang; Sun, Shengjie; Wada, Takehiko; Inoue, Yoshihisa

doi:10.1021/jo981891k

Cited by 105 publications

(54 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The effective stability constant (K s ) 21 can be obtained from the analysis of the sequential changes of fluorescence intensity (F-F 0 ) at various host concentration, using a nonlinear least-squares method according to the curve-fitting equation 22,23 ( ) ( )…”

Section: Apparent Association Constantmentioning

confidence: 99%

Study on the Supramolecular Interaction of β‐Cyclodextrin with Gemfibrozil by Spectrofluorimetry and Its Analytical Application

et al. 2007

View full text Add to dashboard Cite

The supramolecular interaction of gemfibrozil with β-cyclodextrin (β-CD) was studied by spectrofluorimetry. The mechanism of the inclusion was discussed by spectrofluoremetry, infrared spectrum and 1 H NMR spectrum.The results showed that a 1∶1 (β-CD∶gemfibrozil) complex was formed with an apparent association constant of 3.844×10 3 L•mol -1 . Based on the enhancement of the fluorescent intensity of gemfibrozil, a spectrofluorimetric method for the determination of gemfibrozil in bulk aqueous solution in the presence of β-CD was developed. The linear range was 3.30 ng•mL -1 -6.00 µg•mL -1 with the detection limit of 0.980 ng•mL -1 . There was no interference from the excipients normally used in tablet composition and the serum main compositions. The proposed method was then successfully applied to the determination of gemfibrozil in capsules and serum.

show abstract

Section: Apparent Association Constantmentioning

confidence: 99%

Study on the Supramolecular Interaction of β‐Cyclodextrin with Gemfibrozil by Spectrofluorimetry and Its Analytical Application

et al. 2007

View full text Add to dashboard Cite

show abstract

“…In our research, in the case of 1:1 complexation, K was evaluated by the nonlinear curve fitting function that was described in the literature [35]. …”

Section: Stoichiometry and Inclusion Constantmentioning

confidence: 99%

Spectroscopic studies on the inclusion interaction of p-sulfonatocalix[6]arene with vitamin B6

Song

Chao

et al. 2011

J Incl Phenom Macrocycl Chem

View full text Add to dashboard Cite

The formation of the inclusion complex of p-sulfonatocalix[6]arene (SCX6) with different forms of vitamin B 6 (VB 6 ) was studied by using fluorescence spectroscopy. VB 6 can exist in one of three forms (the acidic form, neutral zwitterionic form and basic form) depending on pH. The fluorescence intensities of acidic and basic forms of VB 6 remarkably decreased in presence of SCX6. SCX6 preferred to form 1:1 inclusion complexes with acidic and basic forms of VB 6 but hardly form inclusion complex with neutral zwitterionic form. According to the nonlinear curve fitting method, the inclusion constant (K) for the formation of inclusion complexes of acidic and basic forms of VB 6 with SCX6 were evaluated to be 1.4 9 10 4 and 9 9 10 3 L/mol, respectively. The binding affinity of SCX6 towards acidic form is attributed to hydrogen bonds and hydrophobic interaction, furthermore, additional electrostatic interaction also plays a crucial role. The possible inclusion mode was given by 1 H NMR technique.

show abstract

“…1,2 In the context of the supramolecular chemistry, due to its singular architecture, CDs can be used in a large number of molecular devices such as molecular reactors, 3,4 molecular nanotubes, [5][6][7][8] molecular wires [9][10][11] and also in molecular recognition processes. [12][13][14][15][16] Over several decades, the encapsulating phenomena of low molecular weight compounds by CDs have been subject of numerous investigations 17,18 attracting the attention of the scientific community interested in this research area. In the beginning of the 1990s, there were a limited number of works concerning the threading of polymers with CDs.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of α-CD based [3] pseudorotaxanes: the role played by threadlike polymer on the stability of Cyclodextrin dimers

Anconi¹,

Nascimento²,

Almeida³

et al. 2008

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

As interações entre ciclodextrinas e seus agregados com cadeias poliméricas, têm atraído a atenção de pesquisadores em diferentes subáreas da química supramolecular. Esses compostos, conhecidos como "necklaces", podem ser empregados na formulação de fios e nanotubos moleculares. No presente artigo a formação de dímeros de -CD foi estudada teoricamente considerando as três possíveis orientações relativas, denominadas "head-to-head" (HH), "tail-totail" (TT) e "head-to-tail" (HT). A influência da cadeia polimérica na estabilidade relativa das diferentes associações foi avaliada através do estudo dos compostos de inclusão de ( -CD) 2 com oligo(etilenoglicol) (OEG). Os resultados mostram que a orientação relativa das CDs é definida, primeiramente, pelas interações intermoleculares entre as unidades de -CD, tendo a cadeia polimérica um papel secundário no processo de agregação.Cyclodextrins (CDs) and polymeric chains have attracted considerable attention, being addressed in the literature as novel molecular assembly. The so-called "Molecular Necklace" synthesized by the inclusion of a polymeric chain inside CDs cavity has been employed in the formulation of molecular wires and nanotubes. In this paper we applied our previous reported mixed basis set approach in order to investigate theoretically the -CD inclusion complexes formed by two CD units and an oligo(ethylene glycol) (OEG). In attempt to analyze the role played by the OEG in the formation of pseudo-rotaxane in gas-phase, DFT calculations were performed for six possible dimer associations of CDs, named head-to-head (HH), tail-to-tail (TT) and head-to-tail (HT) with or without an OEG threadlike molecule included in the cavity formed by the -CD dimer. The comparison between relative energies of empty (HH, TT and HT) and filled associations (HH-OEG, TT-OEG and HT-OEG) shows that the OEG chain does not interfere significantly in the relative stabilization energies of the supramolecular systems, therefore the relative arrangements of CDs in the necklace structures should be primarily driven by interactions between cyclodextrin units. Keywords: DFT, alpha cyclodextrin, dimer, OEG, inclusion complex IntroductionCyclodextrin (CD) is a cyclic oligomer of -D-glucose obtained by the action of certain enzymes on starch. Generally described as shallow truncated cones, this class of carbohydrate presents a hydrophobic cavity of different sizes, depending on the number of elementary glucose units. In addition, the structure of the CD molecule possess two different rims, a wider (head) containing all secondary hydroxyl groups and a narrower (tail) containing all primary hydroxyl groups. There are three natural cyclodextrins readily available having six, seven or eight glucose units named -CD, -CD and -CD, respectively.The applications of CDs in supramolecular chemistry have been widely addressed in the literature and the applicability of this class of carbohydrate is closely related to its ability to form inclusion compounds with a very wide range of guest molecules in aqueo...

show abstract

Molecular Recognition Study on Supramolecular Systems. 20. Molecular Recognition and Enantioselectivity of Aliphatic Alcohols by l-Tryptophan-Modified β-Cyclodextrin

Cited by 105 publications

References 28 publications

Study on the Supramolecular Interaction of β‐Cyclodextrin with Gemfibrozil by Spectrofluorimetry and Its Analytical Application

Study on the Supramolecular Interaction of β‐Cyclodextrin with Gemfibrozil by Spectrofluorimetry and Its Analytical Application

Spectroscopic studies on the inclusion interaction of p-sulfonatocalix[6]arene with vitamin B6

Theoretical study of α-CD based [3] pseudorotaxanes: the role played by threadlike polymer on the stability of Cyclodextrin dimers

Contact Info

Product

Resources

About