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dc.contributor.author
Pusterla, Ivano
dc.contributor.author
Bode, Jeffrey W.
dc.date.accessioned
2021-03-05T15:07:23Z
dc.date.available
2021-03-05T15:04:10Z
dc.date.available
2021-03-05T15:07:23Z
dc.date.issued
2015-08
dc.identifier.issn
1755-4349
dc.identifier.issn
1755-4330
dc.identifier.other
10.1038/nchem.2282
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/473256
dc.description.abstract
Amide-forming ligation reactions allow the chemical synthesis of proteins by the union of unprotected peptide segments, and enable the preparation of protein derivatives not accessible by expression or bioengineering approaches. The native chemical ligation (NCL) of thioesters and N-terminal cysteines is unquestionably the most successful approach, but is not ideal for all synthetic targets. Here we describe the synthesis of an Fmoc-protected oxazetidine amino acid for use in the α-ketoacid–hydroxylamine (KAHA) amide ligation. When incorporated at the N-terminus of a peptide segment, this four-membered cyclic hydroxylamine can be used for rapid serine-forming ligations with peptide α-ketoacids. This ligation operates at low concentration (100 μM–5 mM) and mild temperatures (20–25 °C). The utility of the reaction was demonstrated by the synthesis of S100A4, a 12 kDa calcium-binding protein not easily accessible by NCL or other amide-forming reactions due to its primary sequence and properties.
en_US
dc.language.iso
en
en_US
dc.publisher
Nature Publishing Group
en_US
dc.subject
Organic chemistry
en_US
dc.title
An Oxazetidine Amino Acid for Chemical Protein Synthesis by Rapid, Serine-Forming Ligations
en_US
dc.type
Journal Article
dc.date.published
2015-06-22
ethz.journal.title
Nature Chemistry
ethz.journal.volume
7
en_US
ethz.journal.issue
8
en_US
ethz.journal.abbreviated
Nat Chem
ethz.pages.start
668
en_US
ethz.pages.end
672
en_US
ethz.grant
Chemoselective Protein Ligation
en_US
ethz.identifier.wos
ethz.identifier.scopus
ethz.publication.place
London
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::03861 - Bode, Jeffrey W. / Bode, Jeffrey W.
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::03861 - Bode, Jeffrey W. / Bode, Jeffrey W.
ethz.grant.agreementno
150073
ethz.grant.fundername
SNF
ethz.grant.funderDoi
10.13039/501100001711
ethz.grant.program
Projektförderung in Mathematik, Natur- und Ingenieurwissenschaften (Abteilung II)
ethz.date.deposited
2017-06-11T18:36:16Z
ethz.source
ECIT
ethz.identifier.importid
imp5936542d4c9e570199
ethz.identifier.importid
imp5936535c593e278302
ethz.ecitpid
pub:175426
ethz.ecitpid
pub:161118
ethz.eth
yes
en_US
ethz.availability
Metadata only
en_US
ethz.rosetta.installDate
2021-03-05T15:04:22Z
ethz.rosetta.lastUpdated
2021-03-05T15:04:22Z
ethz.rosetta.exportRequired
true
ethz.rosetta.versionExported
true
dc.identifier.olduri
http://hdl.handle.net/20.500.11850/164487
dc.identifier.olduri
http://hdl.handle.net/20.500.11850/102954
ethz.COinS
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