Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (<i<S</i<-CSA) and methyl orange dye depending on the nature of the substituent, result...
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Gespeichert in:

Autor*in:	Anastasia Nazarova [verfasserIn] Dmitriy Shurpik [verfasserIn] Pavel Padnya [verfasserIn] Timur Mukhametzyanov [verfasserIn] Peter Cragg [verfasserIn] Ivan Stoikov [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2020

Schlagwörter:	aggregation (1S)-(+)-10-camphorsulfonic acid host-guest systems methyl orange dye amino acid pillar[5]arene

Übergeordnetes Werk:	In: International Journal of Molecular Sciences - MDPI AG, 2003, 21(2020), 19, p 7206
Übergeordnetes Werk:	volume:21 ; year:2020 ; number:19, p 7206

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc Journal toc

DOI / URN:	10.3390/ijms21197206

Katalog-ID:	DOAJ003565688

Internformat


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spelling	10.3390/ijms21197206 doi (DE-627)DOAJ003565688 (DE-599)DOAJdad719abc41344e38ad63ec32e1c6e13 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Anastasia Nazarova verfasserin aut Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (<i<S</i<-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and <sup<1</sup<H NMR spectroscopy. This work demonstrates the first case of using <i<S</i<-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of <i<S</i<-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels. aggregation (1S)-(+)-10-camphorsulfonic acid host-guest systems methyl orange dye amino acid pillar[5]arene Biology (General) Chemistry Dmitriy Shurpik verfasserin aut Pavel Padnya verfasserin aut Timur Mukhametzyanov verfasserin aut Peter Cragg verfasserin aut Ivan Stoikov verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 21(2020), 19, p 7206 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:21 year:2020 number:19, p 7206 https://doi.org/10.3390/ijms21197206 kostenfrei https://doaj.org/article/dad719abc41344e38ad63ec32e1c6e13 kostenfrei https://www.mdpi.com/1422-0067/21/19/7206 kostenfrei https://doaj.org/toc/1661-6596 Journal toc kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 21 2020 19, p 7206
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allfieldsSound	10.3390/ijms21197206 doi (DE-627)DOAJ003565688 (DE-599)DOAJdad719abc41344e38ad63ec32e1c6e13 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Anastasia Nazarova verfasserin aut Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes 2020 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (<i<S</i<-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and <sup<1</sup<H NMR spectroscopy. This work demonstrates the first case of using <i<S</i<-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of <i<S</i<-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels. aggregation (1S)-(+)-10-camphorsulfonic acid host-guest systems methyl orange dye amino acid pillar[5]arene Biology (General) Chemistry Dmitriy Shurpik verfasserin aut Pavel Padnya verfasserin aut Timur Mukhametzyanov verfasserin aut Peter Cragg verfasserin aut Ivan Stoikov verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 21(2020), 19, p 7206 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:21 year:2020 number:19, p 7206 https://doi.org/10.3390/ijms21197206 kostenfrei https://doaj.org/article/dad719abc41344e38ad63ec32e1c6e13 kostenfrei https://www.mdpi.com/1422-0067/21/19/7206 kostenfrei https://doaj.org/toc/1661-6596 Journal toc kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 21 2020 19, p 7206
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callnumber-first	Q - Science
author	Anastasia Nazarova
spellingShingle	Anastasia Nazarova misc QH301-705.5 misc QD1-999 misc aggregation misc (1S)-(+)-10-camphorsulfonic acid misc host-guest systems misc methyl orange dye misc amino acid misc pillar[5]arene misc Biology (General) misc Chemistry Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes
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topic_title	QH301-705.5 QD1-999 Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes aggregation (1S)-(+)-10-camphorsulfonic acid host-guest systems methyl orange dye amino acid pillar[5]arene
topic	misc QH301-705.5 misc QD1-999 misc aggregation misc (1S)-(+)-10-camphorsulfonic acid misc host-guest systems misc methyl orange dye misc amino acid misc pillar[5]arene misc Biology (General) misc Chemistry
topic_unstemmed	misc QH301-705.5 misc QD1-999 misc aggregation misc (1S)-(+)-10-camphorsulfonic acid misc host-guest systems misc methyl orange dye misc amino acid misc pillar[5]arene misc Biology (General) misc Chemistry
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title	Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes
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title_full	Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes
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author_browse	Anastasia Nazarova Dmitriy Shurpik Pavel Padnya Timur Mukhametzyanov Peter Cragg Ivan Stoikov
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title_sort	self-assembly of supramolecular architectures by the effect of amino acid residues of quaternary ammonium pillar[5]arenes
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title_auth	Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes
abstract	Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (<i<S</i<-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and <sup<1</sup<H NMR spectroscopy. This work demonstrates the first case of using <i<S</i<-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of <i<S</i<-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels.
abstractGer	Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (<i<S</i<-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and <sup<1</sup<H NMR spectroscopy. This work demonstrates the first case of using <i<S</i<-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of <i<S</i<-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels.
abstract_unstemmed	Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (<i<S</i<-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and <sup<1</sup<H NMR spectroscopy. This work demonstrates the first case of using <i<S</i<-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of <i<S</i<-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels.
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title_short	Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes
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The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (<i<S</i<-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and <sup<1</sup<H NMR spectroscopy. This work demonstrates the first case of using <i<S</i<-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of <i<S</i<-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. 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Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

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