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dc.contributor.authorHilko, DH
dc.contributor.authorBornaghi, LF
dc.contributor.authorPoulsen, SA
dc.date.accessioned2021-02-25T03:57:08Z
dc.date.available2021-02-25T03:57:08Z
dc.date.issued2019
dc.identifier.issn1934-9270
dc.identifier.doi10.1002/cpnc.86
dc.identifier.urihttp://hdl.handle.net/10072/388116
dc.description.abstractThis unit describes the detailed preparation of 5‐alkynyl‐2ʹ‐halogenated arabinosyl uridine nucleosides (2ʹ‐halo‐ara‐EdU) from uridine. These compounds were synthesized as prospective chemical probes for the detection of DNA synthesis in proliferating cells. Currently, this is the only synthetic methodology reported to access these compounds. The key to success of the synthetic approach was to employ a 3‐N‐nitro‐protecting group to stabilize the required 2ʹ‐triflate nucleoside precursor toward nucleophilic substitution. Several synthetic challenges were overcome to accommodate the combination of a 5‐alkyne and 3‐N‐nitro functional group, including facile introduction and removal of the N‐nitro group, and removal of the sugar acetyl groups under acidic conditions
dc.description.peerreviewedYes
dc.languageEnglish
dc.language.isoeng
dc.publisherWiley
dc.relation.ispartofpagefrome86
dc.relation.ispartofissue1
dc.relation.ispartofjournalCurrent Protocols in Nucleic Acid Chemistry
dc.relation.ispartofvolume77
dc.subject.fieldofresearchChemical sciences
dc.subject.fieldofresearchcode34
dc.subject.keywordsarabinose
dc.subject.keywordschemical probe
dc.subject.keywordsnitro protecting group
dc.subject.keywordsnucleoside
dc.titleSynthesis of 5-Alkynyl Substituted 2ʹ-Arabinosyl 2ʹ-Halogenated Uridine Nucleosides
dc.typeJournal article
dc.type.descriptionC1 - Articles
dcterms.bibliographicCitationHilko, DH; Bornaghi, LF; Poulsen, SA, Synthesis of 5-Alkynyl Substituted 2ʹ-Arabinosyl 2ʹ-Halogenated Uridine Nucleosides, Current Protocols in Nucleic Acid Chemistry, 2019, 77 (1), pp. e86-
dc.date.updated2019-10-08T00:17:33Z
dc.description.versionAccepted Manuscript (AM)
gro.rights.copyright© 2019 John Wiley & Sons, Inc.. This is the peer reviewed version of the following article: Synthesis of 5‐Alkynyl Substituted 2ʹ‐Arabinosyl 2ʹ‐Halogenated Uridine Nucleosides, Current Protocols in Nucleic Acid Chemistry, 77 (1), pp. e86, which has been published in final form at https://doi.org/10.1002/cpnc.86. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving (http://olabout.wiley.com/WileyCDA/Section/id-828039.html)
gro.hasfulltextFull Text
gro.griffith.authorPoulsen, Sally-Ann
gro.griffith.authorHilko, David H.


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