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标题：Molecular Capture and Conformational Change of Diketopiperazines Containing Proline Residues by Epigallocatechin-3-O-gallate in Water
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作者：Takashi Ishizu ; Miku Tokunaga ; Moeka Fukuda 等
期刊名称：Chemical and Pharmaceutical Bulletin
印刷版ISSN：0009-2363
电子版ISSN：1347-5223
出版年度：2021
卷号：69
期号：6
页码：585-589
DOI：10.1248/cpb.c21-00047
出版社：The Pharmaceutical Society of Japan
摘要：The addition of an aqueous solution of diketopiperazine cyclo(Pro-Xxx) (Xxx: amino acid residue) to an aqueous solution of (−)-epigallocatechin-3- O -gallate (EGCg) led to precipitation of the complex of EGCg and cyclo(Pro-Xxx). The molecular capture abilities of cyclo(Pro-Xxx) using EGCg were evaluated by the ratio of the amount of cyclo(Pro-Xxx) included in the precipitates of the complex with EGCg to that of the total cyclo(Pro-Xxx) used. Stronger hydrophobicity of the side chain of the amino acid residue of cyclo(Pro-Xxx) led to a higher molecular capture ability. Furthermore, the molecular capture ability decreased when the side chain of the amino acid residue had a hydrophilic hydroxyl group. When diketopiperazine cyclo(Pro-Xxx), excluding cyclo(D-Pro-L-Ala), was taken into the hydrophobic space formed by the three aromatic A, B, and B′ rings of EGCg, and formed a complex, their conformation was maintained in the hydrophobic space. Based on nuclear Overhauser effect (NOE) measurement, the 3-position methyl group of cyclo(D-Pro-L-Ala) in D 2 O was axial, whereas that of cyclo(L-Pro-L-Ala) was equatorial. When cyclo(D-Pro-L-Ala) was taken into the hydrophobic space of EGCg and formed a 2 : 2 complex, its 3-position methyl group changed from the axial position to the equatorial position due to steric hindrance by EGCg.
关键词：(−)-epigallocatechin-3-O-gallate;diketopiperazine;proline residue;hydrophobic space;molecular capture ability;quantitative 1H-NMR