U-Shaped Conformation of Alkyl Chains Bound to a Synthetic Host

Taking it in turn: Despite the high internal strain, the long aliphatic chains of alkyltrimethylammonium ions buried deeply inside the cucurbit[8]uril (CB[8]) cavity adopt a U‐shaped conformation (see X‐ray structure), which is stabilized by electrostatic and van der Waals interactions with the carb...

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Published inAngewandte Chemie (International ed.) Vol. 47; no. 22; pp. 4106 - 4109
Main Authors Ko, Young Ho, Kim, Hyunuk, Kim, Youngkook, Kim, Kimoon
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 19.05.2008
WILEY-VCH Verlag
WILEY‐VCH Verlag
Subjects
alkanes
Alkanes - chemistry
Calorimetry
conformation analysis
Crystallography, X-Ray
cucurbiturils
Fatty Acids - chemistry
host-guest systems
inclusion compounds
Macrocyclic Compounds - chemistry
Molecular Conformation
Nuclear Magnetic Resonance, Biomolecular
Quaternary Ammonium Compounds - chemistry
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Summary:Taking it in turn: Despite the high internal strain, the long aliphatic chains of alkyltrimethylammonium ions buried deeply inside the cucurbit[8]uril (CB[8]) cavity adopt a U‐shaped conformation (see X‐ray structure), which is stabilized by electrostatic and van der Waals interactions with the carbonyl‐laced portal and hydrophobic cavity of CB[8]. This conformation is similar to that of fatty acids bound to fatty acid binding proteins.
Bibliography:http://dx.doi.org/10.1002/anie.200800581
Korean Ministry of Science and Technology (MOST)
ark:/67375/WNG-0B1BTS6N-X
We gratefully acknowledge the CRI Program of the Korean Ministry of Science and Technology (MOST), and the BK 21 Program of the Korean Ministry of Education for support of this work. X-ray diffraction experiments using synchrotron radiation were performed at the Pohang Accelerator Laboratory (beam lines 4A and 6C1) supported by MOST and POSTECH.
ArticleID:ANIE200800581
Korean Ministry of Education
istex:7B7038FC790DEB2A6769131D9F3A83187EDDEA0C
We gratefully acknowledge the CRI Program of the Korean Ministry of Science and Technology (MOST), and the BK 21 Program of the Korean Ministry of Education for support of this work. X‐ray diffraction experiments using synchrotron radiation were performed at the Pohang Accelerator Laboratory (beam lines 4A and 6C1) supported by MOST and POSTECH.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200800581