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Nucleoside und Nucleotide. Teil 8. Synthese von Dinucleotiden mit Thymidin und 1‐(2′‐Desoxy‐β‐D‐ribofuranosyl)‐2(1 H )‐pyridon als Bausteinen
Author(s) -
Gregor Ivan,
Séquin Urs,
Tamm Christoph
Publication year - 1975
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.19750580309
Subject(s) - chemistry , glycosidic bond , nucleoside , oligonucleotide , deoxyribose , reagent , stereochemistry , nucleic acid , thymidine , acetic acid , nucleotide , cleavage (geology) , deoxyadenosine , protecting group , adenosine , biochemistry , organic chemistry , enzyme , dna , fracture (geology) , engineering , gene , geotechnical engineering , alkyl
In order to investigate the stability of 1‐(2′‐deoxy‐β‐D‐ribofuranosyl)‐2(1 H )‐pyridone (Π d , 3 ) under the conditions of oligonucleotide synthesis, the dinucleoside monophosphates (MeOTr)Π d ‐T d ( 9 ) and Π d ‐T d ( 11 ), and the dinucleotides Π d ‐T dp ( 15 ) and pII d ‐T d ( 19 ) were prepared, using various procedures. The N‐glycosidic bond between the deoxyribose and the 2(1 H )‐pyridone proved to be much more labile than the one in the naturally occuring nucleosides. It was partially cleaved in condensation reactions with TPS or MS, but no cleavage was observed when DCC was used. Similarly, the glycosidic linkage was attacked by hot 80% acetic acid, the usual reagent for the removal of a p‐methoxytrityl group in thymidine oligonucleotides. Milder treatment with acetic acid/pyridine 7:3 at 100° removed this protecting group and left the N‐glycoside intact. The compounds prepared were characterized by paper and thin layer chromatography as well as by enzymatic degradation.