An inclusion complex of β-Cyclodextrin-L-Phenylalanine : 1H NMR and molecular docking studies

Sompornpisut, Pornthep, Deechalao, Nutsima and Vongsvivut, Jitraporn 2002, An inclusion complex of β-Cyclodextrin-L-Phenylalanine : 1H NMR and molecular docking studies, ScienceAsia, vol. 28, no. 3, pp. 263-270.

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Title An inclusion complex of β-Cyclodextrin-L-Phenylalanine : 1H NMR and molecular docking studies
Author(s) Sompornpisut, Pornthep
Deechalao, Nutsima
Vongsvivut, Jitraporn
Journal name ScienceAsia
Volume number 28
Issue number 3
Start page 263
End page 270
Total pages 8
Publisher Science Society of Thailand under the Patronage of His Majesty the King
Place of publication Bangkok, Thailand
Publication date 2002-09
ISSN 1513-1874
Keyword(s) β-cyclodextrin
inclusion complex
1H-NMR
molecular docking
Summary An inclusion host-guest complex between β-cyclodextrin (β-CD) and L-phenylalanine (LPhe) was investigated using 1H nuclear magnetic resonance spectroscopy and molecular docking techniques. 1H chemical shift changes of β-CD were used to calculate the stability constant (Kstb) of the complex. On the basis of the Hildebrand-Benesi method, the Kstb of the 1:1 complex in D2O solution at 300 K, pD 7.6 was of 25.5 M-1, implying a fast intermolecular exchange rate process. Interestingly, docking simulation indicates the toroidal space can be occupied by L-Phe with two favorable arrangements. For the predicted model with the higher probability score, the L-Phe aromatic ring is facing to the secondary hydroxyl groups of β-CD. Results from NMR and docking simulation are in good agreement with the x-ray structures of β-CD/L-phenylalanine derivatives.
Language eng
Field of Research 030101 Analytical Spectrometry
Socio Economic Objective 970103 Expanding Knowledge in the Chemical Sciences
HERDC Research category C1.1 Refereed article in a scholarly journal
Persistent URL http://hdl.handle.net/10536/DRO/DU:30038956

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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