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Synthesis of Functionalized Lipids, and Their Use for a Tunable Hydrophobization of Nucleosides and Nucleic Acids
Author(s) -
Korneev Sergei,
Rosemeyer Helmut
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100410
Subject(s) - chemistry , nucleic acid , alkylation , combinatorial chemistry , mitsunobu reaction , alcohol , halogen , thymidine , alkyne , base (topology) , stereochemistry , organic chemistry , dna , biochemistry , catalysis , mathematical analysis , alkyl , mathematics
Two series of functionalized single and double side‐chained lipid molecules ( Schemes 1 and 2 ) were prepared. The compounds carry either terminal COOH, OH, or halogen substituents. Moreover, the double side‐chained lipid 18 carries an internal alkyne functionality. The latter compound was used to hydrophobize thymidine at N(3) by base‐catalyzed alkylation. Additionally, fully protected thymidine, 32 , was N(3) ‐alkylated with the double side‐chained alcohol 9 applying Mitsunobu reaction conditions.