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Cover Picture: Synthesis of T‐705‐Ribonucleoside and T‐705‐Ribonucleotide and Studies of Chemical Stability (ChemMedChem 9/2017)
Author(s) -
Huchting Johanna,
Winkler Matthias,
Nasser Hiba,
Meier Chris
Publication year - 2017
Publication title -
chemmedchem
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201700255
Subject(s) - ribonucleoside , lability , chemistry , ribonucleotide , nucleophile , nucleophilic substitution , derivative (finance) , stereochemistry , combinatorial chemistry , medicinal chemistry , nucleotide , rna , organic chemistry , biochemistry , financial economics , economics , gene , catalysis
The front cover picture shows the unexpected and considerable lability of T‐705‐ribonucleoside. T‐705 is an antiviral agent with activities against numerous RNA viruses. It acts as a nucleobase analogue and is converted to the ribonucleoside 5’‐triphosphate intracellularly. T‐705‐ribonucleoside shows high lability under nucleophilic conditions—even in water! After developing a reliable chemical synthesis, the decomposition was attributed to the presence of the fluorine atom and its tendency to support nucleophilic aromatic substitution. Consequently, the N‐glycosidically attached pyrazine derivative decomposes in aqueous medium which is indispensable in biological studies. More information can be found in the Full Paper by Johanna Huchting, Chris Meier et al. on page 652 in Issue 9, 2017 (DOI: 10.1002/cmdc.201700116).