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Synthesis and Properties of Fluorescent cyclo Sal Nucleotides Based on the Pyrimidine Nucleoside m 5 K and Its 2′,3′‐Dideoxy Analog dm 5 K
Author(s) -
Jessen Henning J.,
Fendrich Wolfgang,
Meier Chris
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500532
Subject(s) - chemistry , prodrug , nucleoside , nucleotide , pyrimidine , hydrolysis , thymidine , stereochemistry , derivative (finance) , phosphate , nucleoside analogue , nucleic acid , fluorescence , biochemistry , in vitro , physics , financial economics , gene , quantum mechanics , economics
The synthesis of the fluorescent thymidine nucleoside analog 5‐methyl‐pyrimidin‐2‐one nucleoside 1 (m 5 K) and that of its 2′,3′‐dideoxy derivative 2 (dm 5 K) are described. Moreover, the conversion of 1 and 2 into the corresponding 3‐methyl‐ cyclo Sal‐phosphate triesters 11 and 12 or an enzyme‐cleavable prodrug 5‐acetoxymethylpropionate‐ cyclo Sal‐phosphate triester 13 , and the fluorescence and hydrolysis properties of these new lipophilic triesters are reported. Finally, the suitability of these cyclo Sal pronucleotides as probes is demonstrated in a cell‐extract hydrolysis experiment and a model study for cell uptake. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)