Competitive Selection of Conformation Chirality of Water-Soluble Pillar[5]arene Induced by Amino Acid Derivatives

The competitive conformation chirality of dynamically racemic water-soluble pillar[5]­arene WP5 can be induced by 19 different l-amino acid ethyl ester hydrochlorides. Among them, l-Arg-OEt and 18 other l-amino acid ethyl ester hydrochlorides can induce the opposite-handedness conformation of WP5. T...

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Published inOrganic letters Vol. 22; no. 6; pp. 2266 - 2270
Main Authors Chen, Yuan, Fu, Lulu, Sun, Baobao, Qian, Cheng, Wang, Ruibing, Jiang, Juli, Lin, Chen, Ma, Jing, Wang, Leyong
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 20.03.2020
Subjects
amino acid derivatives
amino acids
aromatic hydrocarbons
moieties
optical isomerism
water solubility
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Summary:The competitive conformation chirality of dynamically racemic water-soluble pillar[5]­arene WP5 can be induced by 19 different l-amino acid ethyl ester hydrochlorides. Among them, l-Arg-OEt and 18 other l-amino acid ethyl ester hydrochlorides can induce the opposite-handedness conformation of WP5. This was ascribed to the different binding models with a side-chain moiety or ethyl ester moiety of amino acids toward the cavity of WP5.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c00468