Synthesis of Thymidine, Uridine, and 5-Methyluridine Nucleolipids: Tools for a Tuned Lipophilization of Oligonucleotides

Autor(en): Werz, Emma
Viere, Rebecca
Gassmann, Gina
Korneev, Sergei 
Malecki, Edith
Rosemeyer, Helmut 
Stichwörter: Chemistry; Chemistry, Multidisciplinary; Lipophilization; MITSUNOBU REACTION; NUCLEOSIDES; Oligonucleotides; Pyrimidine nucleosides
Erscheinungsdatum: 2013
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 96
Ausgabe: 5
Startseite: 872
Seitenende: 888
Zusammenfassung: 
Three pyrimidine nucleosides, uridine (1), 5-methyluridine (6), and 2-deoxythymidine (11), were converted to amphiphilic nucleolipids. Compounds 1 and 6 were lipophilized by introduction of symmetric ketal moieties with various carbon chain lengths (i.e., 517). Two ketal derivatives, 2b and 7a, were additionally further hydrophobized by N(3)-farnesylation. 2-Deoxythymidine was alkylated at N(3) with a cetyl (=hexadecyl) residue, either directly or, after complete orthogonal protection of the sugar OH groups, by Mitsunobu reaction with hexadecan-1-ol. Some of the nucleolipids were subsequently converted to their 2-cyanoethyl phosphoramidites (5 or 3), one of which was used for an exemplary synthesis of a lipo-oligonucleotide. The sequence of this lipo-oligonucleotide is an encoded manifestation of Pythagoras' law, created with a key table in which the letters of the alphabet, the numbers from 0 to 9 as well as the mostly used mathematical symbols are allocated to a ribonucleic acid triplet of the genetic code.
ISSN: 0018019X
DOI: 10.1002/hlca.201200573

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