Synthesis of 5-Alkynyl Substituted 2ʹ-Arabinosyl 2ʹ-Halogenated Uridine Nucleosides
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Author(s)
Hilko, DH
Bornaghi, LF
Poulsen, SA
Year published
2019
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This 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 ...
View more >This 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
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View more >This 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
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Journal Title
Current Protocols in Nucleic Acid Chemistry
Volume
77
Issue
1
Copyright Statement
© 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)
Subject
Chemical sciences
arabinose
chemical probe
nitro protecting group
nucleoside