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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)

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Abstract

The solid cyclodextrin (α-, β-CD) inclusion compounds of phenylalanine (D-, L- and DL-Phe) and tryptophan (D-, L-␣and DL-Trp) were prepared and the stoichiometry of host and guest in the supermolecules was determined to be 1:1 based on elemental analyses. β-CD formed inclusion compounds with α-aromatic amino acid (α-AAA) in higher yield in contradistinction to α-CD. The yields of the α- or β-CD inclusion compounds of a pair of optical isomers of chiral aromatic amino acids and their racemic modification decreased in the order L->DL->D-form. The complexation between CD and α-AAA caused a change in shape, location and diffracted intensity of the X-ray diffraction peaks of both host and guest. The decomposition temperature of the inclusion compounds was not only slightly higher than that of a pure host but also remarkably higher than that of a pure guest. Upon inclusion the signals of CD protons inside the cavity shifted to upfield while those of the protons outside the cavity had only smaller changes, and the proton signals of the aromatic ring of guest shifted to a certain extent. The chemical shift changes of 4-H and 5-H located in small end side of cavity were a bit bigger than those of 2-H and 3-H located in large one, suggesting that aromatic ring of a guest molecule within a host cavity might be kept near small end side of␣cavity. An ESI-MS experiment has proved the formation and stability of the 1:1 CD inclusion compounds of α-AAA in aqueous solution.

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Authors and Affiliations

  1. Department of Chemistry, University of Science and Technology of China, 230026, Hefei, China

    Le Xin Song, Chuan Feng Teng & Yan Yang

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  1. Le Xin Song
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  2. Chuan Feng Teng
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  3. Yan Yang
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Correspondence to Le Xin Song.

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Song, L.X., Teng, C.F. & Yang, Y. 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). J Incl Phenom Macrocycl Chem 54, 221–232 (2006). https://doi.org/10.1007/s10847-005-7970-8

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  • DOI: https://doi.org/10.1007/s10847-005-7970-8

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