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Synthesis of 5-substituted 2'-deoxyuridine-5'-phosphonate analogues and evaluation of their antiviral activity

Sara Van Poecke UGent, Davy Sinnaeve UGent, José Martins UGent, Jan Balzarini and Serge Van Calenbergh UGent (2012) NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS. 31(1-3). p.256-272
abstract
A small series of 5-(hetero)aryl-modified nucleoside phosphonates was synthesized via an 8-step procedure including a Wittig reaction and Suzuki-Miyaura coupling. An unanticipated anomerization during phosphonate deprotection allowed us to isolate both anomers of the 5-substituted 2'-deoxy-uridine phosphonates and assess their antiviral activity against a broad panel of viruses.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
antiviral activity, alpha-nucleosides, phosphonates, Antiviral nucleoside analogues, pyrimidine modification
journal title
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Nucleosides Nucleotides Nucleic Acids
volume
31
issue
1-3
pages
256 - 272
Web of Science type
Article
Web of Science id
000302276700021
JCR category
BIOCHEMISTRY & MOLECULAR BIOLOGY
JCR impact factor
0.713 (2012)
JCR rank
271/288 (2012)
JCR quartile
4 (2012)
ISSN
1525-7770
DOI
10.1080/15257770.2012.654876
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
2129197
handle
http://hdl.handle.net/1854/LU-2129197
date created
2012-06-01 15:03:40
date last changed
2013-04-01 00:30:44
@article{2129197,
  abstract     = {A small series of 5-(hetero)aryl-modified nucleoside phosphonates was synthesized via an 8-step procedure including a Wittig reaction and Suzuki-Miyaura coupling. An unanticipated anomerization during phosphonate deprotection allowed us to isolate both anomers of the 5-substituted 2'-deoxy-uridine phosphonates and assess their antiviral activity against a broad panel of viruses.},
  author       = {Van Poecke, Sara and Sinnaeve, Davy and Martins, Jos{\'e} and Balzarini, Jan and Van Calenbergh, Serge},
  issn         = {1525-7770},
  journal      = {NUCLEOSIDES NUCLEOTIDES \& NUCLEIC ACIDS},
  keyword      = {antiviral activity,alpha-nucleosides,phosphonates,Antiviral nucleoside analogues,pyrimidine modification},
  language     = {eng},
  number       = {1-3},
  pages        = {256--272},
  title        = {Synthesis of 5-substituted 2'-deoxyuridine-5'-phosphonate analogues and evaluation of their antiviral activity},
  url          = {http://dx.doi.org/10.1080/15257770.2012.654876},
  volume       = {31},
  year         = {2012},
}

Chicago
Van Poecke, Sara, Davy Sinnaeve, José Martins, Jan Balzarini, and Serge Van Calenbergh. 2012. “Synthesis of 5-substituted 2’-deoxyuridine-5'-phosphonate Analogues and Evaluation of Their Antiviral Activity.” Nucleosides Nucleotides & Nucleic Acids 31 (1-3): 256–272.
APA
Van Poecke, S., Sinnaeve, D., Martins, J., Balzarini, J., & Van Calenbergh, S. (2012). Synthesis of 5-substituted 2’-deoxyuridine-5'-phosphonate analogues and evaluation of their antiviral activity. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 31(1-3), 256–272.
Vancouver
1.
Van Poecke S, Sinnaeve D, Martins J, Balzarini J, Van Calenbergh S. Synthesis of 5-substituted 2’-deoxyuridine-5'-phosphonate analogues and evaluation of their antiviral activity. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS. 2012;31(1-3):256–72.
MLA
Van Poecke, Sara, Davy Sinnaeve, José Martins, et al. “Synthesis of 5-substituted 2’-deoxyuridine-5'-phosphonate Analogues and Evaluation of Their Antiviral Activity.” NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS 31.1-3 (2012): 256–272. Print.