1590381-35-3Relevant academic research and scientific papers
Mitsunobu reactions of 5-fluorouridine with the terpenols Phytol and Nerol: DNA building blocks for a biomimetic lipophilization of nucleic acids
Malecki, Edith,Knies, Christine,Werz, Emma,Rosemeyer, Helmut
, p. 2209 - 2220 (2013)
The cancerostatic 5-fluorouridine (5-FUrd; 1) was sequentially sugar-protected by introduction of a 2′,3′-O-heptylidene ketal group (→2), followed by 5′-O-monomethoxytritylation (→3). This fully protected derivative was submitted to Mitsunobu reactions with either phytol ((Z and E)-isomer) or nerol ((Z)-isomer) to yield the nucleoterpenes 4a and 4b. Both were 5′-O-deprotected with 2% Cl2CHCOOH in CH 2Cl2 to yield compounds 5a and 5b, respectively. These were converted to the 5′-O-cyanoethyl phosphoramidites 6a and 6b, respectively. Moreover, the 2′,3′-O-(1-nonyldecylidene) derivative, 7a, of 5-fluorouridine was resynthesized and labelled at C(5′) with an Eterneon-480 fluorophor (→7b). The resulting nucleolipid was studied with respect to its incorporation in an artificial bilayer, as well as to its aggregate formation. Additionally, two oligonucleotides carrying terminal phytol-alkylated 5-fluorouridine tags were prepared, one of which was studied concerning its incorporation in an artificial lipid bilayer. Copyright
