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dc.contributor.author
Geigle, Stefanie N.
dc.contributor.author
Wyss, Laura A.
dc.contributor.author
Sturla, Shana J.
dc.contributor.author
Gillingham, Dennis G.
dc.date.accessioned
2019-06-06T13:32:35Z
dc.date.available
2017-06-12T18:17:00Z
dc.date.available
2019-06-06T13:32:35Z
dc.date.issued
2017-01-01
dc.identifier.issn
2041-6520
dc.identifier.issn
2041-6539
dc.identifier.other
10.1039/C6SC03502G
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/125878
dc.identifier.doi
10.3929/ethz-b-000125878
dc.description.abstract
Cu(I) carbenes derived from α-diazocarbonyl compounds lead to selective alkylation of the O6 position in guanine (O6-G) in mono- and oligonucleotides. Only purine-type lactam oxygens are targeted – other types of amides or lactams are poorly reactive under conditions that give smooth alkylation of guanine. Mechanistic studies point to N7G as a directing group that controls selectivity. Given the importance of O6-G adducts in biology and biotechnology we expect that Cu(I)-catalyzed O6-G alkylation will be a broadly used synthetic tool. While the propensity for transition metals to increase redox damage is well-appreciated, our results suggest that transition metals might also increase the vulnerability of nucleic acids to alkylation damage.
en_US
dc.format
application/pdf
en_US
dc.language.iso
en
en_US
dc.publisher
Royal Society of Chemistry
en_US
dc.rights.uri
http://creativecommons.org/licenses/by-nc/3.0/
dc.title
Copper carbenes alkylate guanine chemoselectively through a substrate directed reaction
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution-NonCommercial 3.0 Unported
dc.date.published
2016-09-07
ethz.journal.title
Chemical Science
ethz.journal.volume
8
en_US
ethz.journal.issue
1
en_US
ethz.journal.abbreviated
Chem. sci.
ethz.pages.start
499
en_US
ethz.pages.end
506
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.grant
DNA Alkylation and Resistance in Antitumor Drug Toxicity
en_US
ethz.identifier.wos
ethz.identifier.scopus
ethz.identifier.nebis
010587385
ethz.publication.place
Cambridge
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02070 - Dep. Gesundheitswiss. und Technologie / Dep. of Health Sciences and Technology::02701 - Inst.f. Lebensmittelwiss.,Ernährung,Ges. / Institute of Food, Nutrition, and Health::03853 - Sturla, Shana / Sturla, Shana
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02070 - Dep. Gesundheitswiss. und Technologie / Dep. of Health Sciences and Technology::02701 - Inst.f. Lebensmittelwiss.,Ernährung,Ges. / Institute of Food, Nutrition, and Health::03853 - Sturla, Shana / Sturla, Shana
en_US
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02070 - Dep. Gesundheitswiss. und Technologie / Dep. of Health Sciences and Technology::02701 - Inst.f. Lebensmittelwiss.,Ernährung,Ges. / Institute of Food, Nutrition, and Health::03853 - Sturla, Shana / Sturla, Shana
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02070 - Dep. Gesundheitswiss. und Technologie / Dep. of Health Sciences and Technology::02701 - Inst.f. Lebensmittelwiss.,Ernährung,Ges. / Institute of Food, Nutrition, and Health::03853 - Sturla, Shana / Sturla, Shana
ethz.grant.agreementno
156280
ethz.grant.fundername
SNF
ethz.grant.funderDoi
10.13039/501100001711
ethz.grant.program
ethz.date.deposited
2017-06-12T18:17:12Z
ethz.source
ECIT
ethz.identifier.importid
imp5936551734a7d17791
ethz.ecitpid
pub:188528
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2017-07-26T07:00:04Z
ethz.rosetta.lastUpdated
2020-02-15T19:27:29Z
ethz.rosetta.versionExported
true
ethz.COinS
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