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dc.contributor.author
Chak, Man Him
dc.contributor.author
Schnurr, Martin
dc.contributor.author
Lewandowski, Bartosz
dc.date.accessioned
2023-09-12T14:00:44Z
dc.date.available
2023-06-24T05:59:30Z
dc.date.available
2023-06-26T06:48:41Z
dc.date.available
2023-09-12T14:00:44Z
dc.date.issued
2023-06-17
dc.identifier.issn
1434-193X
dc.identifier.issn
1099-0690
dc.identifier.other
10.1002/ejoc.202300305
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/618132
dc.identifier.doi
10.3929/ethz-b-000618132
dc.description.abstract
Amino acids are important biomolecules with a broad scope of applications in chemical and biological sciences. Their functions and properties depend on their absolute configuration. Therefore, methods for chiral recognition and separation of amino acids are highly sought after. For the purposes of diagnostic and medicinal applications chiral recognition of amino acids in water is particularly relevant. However synthetic receptors for enantioselective binding of amino acids in aqueous media are rare. Recently we reported a d-glucose-based crown ether for chiral recognition of amino acid esters in water. We achieved enantioselectivities towards amino acids with hydrophobic sidechains which were among the highest ever reported for a small molecule receptor. The binding affinities were however moderate. Herein we disclose analogs of that receptor, containing aryl functionalities in the crown ether fragment. The new receptors show considerably improved binding affinities for amino acid ester hydrochlorides in water, while retaining high enantio- or chemoselectivities.
en_US
dc.format
application/pdf
en_US
dc.language.iso
en
en_US
dc.publisher
Wiley-VCH
en_US
dc.rights.uri
http://creativecommons.org/licenses/by-nc/4.0/
dc.subject
amino-acids
en_US
dc.subject
chiral recognition
en_US
dc.subject
macrocycles
en_US
dc.subject
monosaccharides
en_US
dc.subject
supramolecular chemistry
en_US
dc.title
Aryl Crown Ethers Based on d-Glucose Scaffold - Highly Selective Receptors of Amino Acid Ester Hydrochlorides
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution-NonCommercial 4.0 International
dc.date.published
2023-05-31
ethz.journal.title
European Journal of Organic Chemistry
ethz.journal.volume
26
en_US
ethz.journal.issue
27
en_US
ethz.journal.abbreviated
Eur. j. org. chem.
ethz.pages.start
e202300305
en_US
ethz.size
9 p.
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.identifier.wos
ethz.identifier.scopus
ethz.publication.place
Weinheim
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03940 - Wennemers, Helma / Wennemers, Helma
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03940 - Wennemers, Helma / Wennemers, Helma
ethz.date.deposited
2023-06-24T05:59:34Z
ethz.source
WOS
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2023-09-12T14:00:46Z
ethz.rosetta.lastUpdated
2024-02-03T03:27:04Z
ethz.rosetta.versionExported
true
ethz.COinS
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