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- Title
Nucleotides. Part LIV. Synthesis of condensed N<sup>1</sup>-(2′-deoxy-β- D-ribofuranosyl)lumazines, New fluorescent building blocks in oligonucleotide synthesis.
- Authors
Rosler, Angelika; Pfleiderer, Wolfgang
- Abstract
Various condensed areno[ g]lumazine derivatives 2, 3, and 5- 7 were synthesized as new fluorescent aglycones for glycosylation reactions with 2-deoxy-3, 5-di- O-( p-toluoyl)-α/β- D- erythro-pentofuranosyl chloride ( 10) to form, in a Hilbert- Johnson- Birkofer reaction, the corresponding N1-(2′-deoxyribonucleosides) 15- 21. The β- D-anomers 15, 17, 19, and 21 were deblocked to 24- 27 and, together with N1-(2′-deoxy-β- D-ribofuranosyl)lumazine ( 22) and its 6, 7-diphenyl derivative 23, dimethoxytritylated in 5′-position to 28-33. These intermediates were then converted into the 3′-(2-cyanoethyI diisopropylphosphoramidites) 34- 39 which function as monomeric building block in oligonucleotide syntheses as well as into the 3′-(hydrogen succinates) 40- 45 which can be used for coupling with the solid-support material. A series of lumazine-modified oligonucleotides were synthesized and the influence of the new nucleobases on the stability of duplex formation studied by measuring the Tm values in comparison to model sequences. A substantial increase in the Tm is observed on introduction of areno[ g]lumazine moieties in the oligonucleotide chain stabilizing obviously the helical structures by improved stacking effects. Stabilization is strongly dependent on the site of the modified nucleobase in the chain.
- Publication
Helvetica Chimica Acta, 1997, Vol 80, Issue 6, p1869
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19970800611