PMID- 31125509
OWN - NLM
STAT- MEDLINE
DCOM- 20191213
LR  - 20191217
IS  - 1934-9289 (Electronic)
IS  - 1934-9270 (Linking)
VI  - 77
IP  - 1
DP  - 2019 Jun
TI  - Synthesis of 5-Alkynyl Substituted 2'-Arabinosyl 2'-Halogenated Uridine 
      Nucleosides.
PG  - e86
LID - 10.1002/cpnc.86 [doi]
AB  - This unit describes the detailed preparation of 5-alkynyl-2'-halogenated 
      arabinosyl uridine nucleosides (2'-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 2'-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. (c) 2019 by John Wiley & Sons, Inc.
CI  - (c) 2019 John Wiley & Sons, Inc.
FAU - Hilko, David H
AU  - Hilko DH
AD  - Griffith Institute for Drug Discovery, Griffith University, Nathan, Brisbane, 
      Queensland, Australia.
FAU - Bornaghi, Laurent F
AU  - Bornaghi LF
AD  - Griffith Institute for Drug Discovery, Griffith University, Nathan, Brisbane, 
      Queensland, Australia.
FAU - Poulsen, Sally-Ann
AU  - Poulsen SA
AD  - Griffith Institute for Drug Discovery, Griffith University, Nathan, Brisbane, 
      Queensland, Australia.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20190524
PL  - United States
TA  - Curr Protoc Nucleic Acid Chem
JT  - Current protocols in nucleic acid chemistry
JID - 101287865
RN  - 0 (Alkynes)
RN  - 0 (Halogens)
RN  - 0 (Molecular Probes)
RN  - 0 (Nucleosides)
RN  - WHI7HQ7H85 (Uridine)
SB  - IM
MH  - Alkynes/*chemistry
MH  - Halogens/*chemistry
MH  - Molecular Probes
MH  - Nucleosides/*chemical synthesis/chemistry
MH  - Spectrum Analysis/methods
MH  - Uridine/*chemistry
OTO - NOTNLM
OT  - arabinose
OT  - chemical probe
OT  - nitro protecting group
OT  - nucleoside
EDAT- 2019/05/28 06:00
MHDA- 2019/12/18 06:00
CRDT- 2019/05/25 06:00
PHST- 2019/05/28 06:00 [pubmed]
PHST- 2019/12/18 06:00 [medline]
PHST- 2019/05/25 06:00 [entrez]
AID - 10.1002/cpnc.86 [doi]
PST - ppublish
SO  - Curr Protoc Nucleic Acid Chem. 2019 Jun;77(1):e86. doi: 10.1002/cpnc.86. Epub 
      2019 May 24.