Impact of the β-turn hydrogen bond on the trans/cis ratio and the performance of the peptide catalyst H-dPro-Pro-Glu-NH2
dc.contributor.author
Schnitzer, Tobias
dc.contributor.author
Ganzoni, Rudolf L.
dc.contributor.author
Wennemers, Helma
dc.date.accessioned
2021-01-08T10:55:18Z
dc.date.available
2020-12-24T03:41:04Z
dc.date.available
2021-01-08T10:55:18Z
dc.date.issued
2020-12-18
dc.identifier.issn
0040-4020
dc.identifier.other
10.1016/j.tet.2020.131184
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/458488
dc.description.abstract
The effect of the β-turn hydrogen bond on the trans/cis conformer ratio and the catalytic performance of the peptidic catalyst H-dPro-Pro-Glu-NH2 was investigated. Different electron withdrawing and donating substituents at the C-terminus of peptide analogues caused changes in the trans/cis ratio and the enantioselectivities of the peptides in conjugate addition reactions of aldehydes to nitroolefins. The results imply that the β-turn H-bond contributes but is not critical for the catalytic performance of H-dPro-Pro-Glu-NH2 and related peptidic catalysts. © 2020 Elsevier
en_US
dc.language.iso
en
en_US
dc.publisher
Elsevier
en_US
dc.subject
Peptide catalysis
en_US
dc.subject
Conjugate addition reaction
en_US
dc.subject
Conformational analysis of peptides
en_US
dc.subject
trans/cis isomerization
en_US
dc.subject
β-turn peptides
en_US
dc.title
Impact of the β-turn hydrogen bond on the trans/cis ratio and the performance of the peptide catalyst H-dPro-Pro-Glu-NH2
en_US
dc.type
Journal Article
dc.date.published
2020-04-16
ethz.journal.title
Tetrahedron
ethz.journal.volume
76
en_US
ethz.journal.issue
51
en_US
ethz.journal.abbreviated
Tetrahedron (Oxf., Print)
ethz.pages.start
131184
en_US
ethz.size
5 p.
en_US
ethz.grant
Bioinspirierte Asymmetrische Katalyse (Fortsetzung 2020)
en_US
ethz.identifier.wos
ethz.identifier.scopus
ethz.publication.place
Amsterdam
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
en_US
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.grant.agreementno
188729
ethz.grant.fundername
SNF
ethz.grant.funderDoi
10.13039/501100001711
ethz.grant.program
Projekte MINT
ethz.date.deposited
2020-12-24T03:41:17Z
ethz.source
SCOPUS
ethz.eth
yes
en_US
ethz.availability
Metadata only
en_US
ethz.rosetta.installDate
2021-01-08T10:55:27Z
ethz.rosetta.lastUpdated
2022-03-29T04:44:27Z
ethz.rosetta.versionExported
true
ethz.COinS
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Journal Article [120884]