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Synthesis of Methylenecyclobutane Analogues of Nucleosides with Axial Chirality and Their Phosphoralaninates: A New Pronucleotide Effective against Epstein-Barr Virus:

Synthesis of Methylenecyclobutane Analogues of Nucleosides with Axial Chirality and Their... Methylenecyclobutane analogues of 2′-deoxyadenosine, 2′-deoxyguanosine and 2′- deoxycytidine, and the corresponding phosphoralaninate pronucleotides comprising adenine and guanine bases, were synthesized as potential antiviral agents. Phosphoralaninate of adenine methylenecyclobutane was a potent inhibitor of replication of Epstein-Barr virus (EBV) in Daudi cell culture. Phosphoralaninate of guanine analogue was inactive but both pronucleotides were substrates for porcine liver esterase. Adenine methylenecyclobutane analogue was deaminated by adenosine deaminase. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Antiviral Chemistry and Chemotherapy SAGE

Synthesis of Methylenecyclobutane Analogues of Nucleosides with Axial Chirality and Their Phosphoralaninates: A New Pronucleotide Effective against Epstein-Barr Virus:

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Publisher
SAGE
Copyright
Copyright © 2019 by SAGE Publications Ltd unless otherwise noted. Manuscript content on this site is licensed under Creative Commons Licenses
ISSN
2040-2066
eISSN
2040-2066
DOI
10.1177/095632020201300406
Publisher site
See Article on Publisher Site

Abstract

Methylenecyclobutane analogues of 2′-deoxyadenosine, 2′-deoxyguanosine and 2′- deoxycytidine, and the corresponding phosphoralaninate pronucleotides comprising adenine and guanine bases, were synthesized as potential antiviral agents. Phosphoralaninate of adenine methylenecyclobutane was a potent inhibitor of replication of Epstein-Barr virus (EBV) in Daudi cell culture. Phosphoralaninate of guanine analogue was inactive but both pronucleotides were substrates for porcine liver esterase. Adenine methylenecyclobutane analogue was deaminated by adenosine deaminase.

Journal

Antiviral Chemistry and ChemotherapySAGE

Published: Jun 23, 2016

Keywords: methylenecyclobutane analogues of nucleosides,phosphoralaninates,pronucleotides,EBV,porcine liver esterase,adenosine deaminase

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