𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Nucleotides. Part LIV. Synthesis of condensed N1-(2′-deoxy-β-D-ribofuranosyl)lumazines, New fluorescent building blocks in oligonucleotide synthesis

✍ Scribed by Angelika Rosler; Wolfgang Pfleiderer

Publisher
John Wiley and Sons
Year
1997
Tongue
German
Weight
924 KB
Volume
80
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Dedicated with best personal wishes to Prof. Dieter Seebach on the occasion of his 60th birthday (2.VII.97) Various condensed arenok]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)-a/~-~-erythranosyl chloride (10) to form, in a Hilbert-Johnson-Birkofer reaction, the corresponding N'-(Z-deoxyribonucleosides) 15-21. The b-D-anomers 15, 17,19, and 21 were deblocked to 24-27 and, together with N1-(2'-deoxy-@-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-cyanoethyl diisopropylphosphoramidites) 34-39 which function as monomeric building block in oligonucleotide syntheses as well as into the 3'-(hydrogen succinates) 4 -4 5 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 T,,, values in comparison to model sequences. A substantial increase in the T,,, is observed on introduction of arenokllumazine 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. ' 1 Part LIII: [I].

📜 SIMILAR VOLUMES

ChemInform Abstract: Nucleotides. Part 5
ChemInform Abstract: Nucleotides. Part 54. Synthesis of Condensed N1-(2′-Deoxy-β-D- ribofuranosyl)lumazines, New Fluorescent Building Blocks in Oligonucleotide Synthesis.
✍ A. ROESLER; W. PFLEIDERER 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

Nucleotides. Part 54. Synthesis of Condensed N1-(2'-Deoxy-β-D-ribofuranosyl)lumazines, New Fluorescent Building Blocks in Oligonucleotide Synthesis. -Various condensed areno(g)lumazine derivatives (III) and (VI) are synthesized as new fluorescent aglycones for glycosylation reactions to form differe

Nucleic Acid Analogs with Constraint Con
Nucleic Acid Analogs with Constraint Conformational Flexibility in the Sugar-Phosphate Backbone “Tricyclo-DNA”. Part 1. Preparation of [(5′R,6′R)-2′-deoxy-3′,5′-ethano-5′,6′-methano-β-D-ribofuranosyl]thymine and -adenine, and the corresponding phosphoramidites for oligonucleotide synthesis
✍ Ralph Steffans; Christian Leumann 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 German ⚖ 1019 KB

In extension of the bicyclo-DNA nomenclature (see , Foornote 3), the name tricyclo-DNA and, correspondingly, tricyclo-deoxynucleosides was chosen to denominate this type of nucleotide and nucleoside analog. ## The numbering scheme as depicted in Fig. f for nucleosides was chosen in order to be ab

ChemInform Abstract: Nucleic-Acid Analog
ChemInform Abstract: Nucleic-Acid Analogues with Constraint Conformational Flexibility in the Sugar—Phosphate Backbone ′Tricyclo-DNA′. Part 1. Preparation of [(5′R,6′R)-2′-Deoxy-3′,5′-ethano-5′,6′-methano-β-D-ribofuranosyl] thymine and -adenine, and the Corresponding Phosphoramidites for Oligonucleotide Synthesis.
✍ R. STEFFENS; C. LEUMANN 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 39 KB 👁 1 views

Nucleic-Acid Analogues with Constraint Conformational Flexibility in the Sugar-Phosphate Backbone 'Tricyclo-DNA'. Part 1. Preparation of [(5'R,6'R)-2'-Deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl] thymine and -adenine, and the Corresponding Phosphoramidites for Oligonucleotide Synthesis. -An