Terminal Trialkylsilyl Substituent Effect of Janus-type Molecular Tubes on the Inclusion of Unsaturated Fatty Acid Esters

[Image: see text] A new Janus-type cyclodextrin (CD) molecular tube bearing seven triisopropylsilyl (TIPS) groups at one end is synthesized from a heptakis(6-O-triisopropylsilyl)-β-cyclodextrin (TIPS-β-CD) dimer possessing multiple linkers through the selective removal of seven TIPS groups at the ot...

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Autores principales: Kogame-Asahara, Chizuru, Iguchi, Hitomi, Honda, Kenichiro, Shigemitsu, Hajime, Kida, Toshiyuki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7860515/
https://www.ncbi.nlm.nih.gov/pubmed/33553939
http://dx.doi.org/10.1021/acsomega.0c05672
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author Kogame-Asahara, Chizuru
Iguchi, Hitomi
Honda, Kenichiro
Shigemitsu, Hajime
Kida, Toshiyuki
author_facet Kogame-Asahara, Chizuru
Iguchi, Hitomi
Honda, Kenichiro
Shigemitsu, Hajime
Kida, Toshiyuki
author_sort Kogame-Asahara, Chizuru
collection PubMed
description [Image: see text] A new Janus-type cyclodextrin (CD) molecular tube bearing seven triisopropylsilyl (TIPS) groups at one end is synthesized from a heptakis(6-O-triisopropylsilyl)-β-cyclodextrin (TIPS-β-CD) dimer possessing multiple linkers through the selective removal of seven TIPS groups at the other end. This Janus-type CD tube exhibits a selective inclusion ability for a cis-fatty acid ester over the corresponding trans-fatty acid ester. In addition, the CD tube shows a twofold higher inclusion ability for unsaturated fatty acid esters than the corresponding CD tube bearing seven tert-butyldimethylsilyl (TBDMS) groups, indicating that the molecular size of the terminal substituents remarkably affects the inclusion ability of the CD tube.
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spelling pubmed-78605152021-02-05 Terminal Trialkylsilyl Substituent Effect of Janus-type Molecular Tubes on the Inclusion of Unsaturated Fatty Acid Esters Kogame-Asahara, Chizuru Iguchi, Hitomi Honda, Kenichiro Shigemitsu, Hajime Kida, Toshiyuki ACS Omega [Image: see text] A new Janus-type cyclodextrin (CD) molecular tube bearing seven triisopropylsilyl (TIPS) groups at one end is synthesized from a heptakis(6-O-triisopropylsilyl)-β-cyclodextrin (TIPS-β-CD) dimer possessing multiple linkers through the selective removal of seven TIPS groups at the other end. This Janus-type CD tube exhibits a selective inclusion ability for a cis-fatty acid ester over the corresponding trans-fatty acid ester. In addition, the CD tube shows a twofold higher inclusion ability for unsaturated fatty acid esters than the corresponding CD tube bearing seven tert-butyldimethylsilyl (TBDMS) groups, indicating that the molecular size of the terminal substituents remarkably affects the inclusion ability of the CD tube. American Chemical Society 2021-01-25 /pmc/articles/PMC7860515/ /pubmed/33553939 http://dx.doi.org/10.1021/acsomega.0c05672 Text en © 2021 The Authors. Published by American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Kogame-Asahara, Chizuru
Iguchi, Hitomi
Honda, Kenichiro
Shigemitsu, Hajime
Kida, Toshiyuki
Terminal Trialkylsilyl Substituent Effect of Janus-type Molecular Tubes on the Inclusion of Unsaturated Fatty Acid Esters
title Terminal Trialkylsilyl Substituent Effect of Janus-type Molecular Tubes on the Inclusion of Unsaturated Fatty Acid Esters
title_full Terminal Trialkylsilyl Substituent Effect of Janus-type Molecular Tubes on the Inclusion of Unsaturated Fatty Acid Esters
title_fullStr Terminal Trialkylsilyl Substituent Effect of Janus-type Molecular Tubes on the Inclusion of Unsaturated Fatty Acid Esters
title_full_unstemmed Terminal Trialkylsilyl Substituent Effect of Janus-type Molecular Tubes on the Inclusion of Unsaturated Fatty Acid Esters
title_short Terminal Trialkylsilyl Substituent Effect of Janus-type Molecular Tubes on the Inclusion of Unsaturated Fatty Acid Esters
title_sort terminal trialkylsilyl substituent effect of janus-type molecular tubes on the inclusion of unsaturated fatty acid esters
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7860515/
https://www.ncbi.nlm.nih.gov/pubmed/33553939
http://dx.doi.org/10.1021/acsomega.0c05672
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