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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geprüft am 21.05.2024