SYNTHESIS OF (2-DEOXY-ALPHA - AND -BETA -D-ERYTHRO-PENTOFURANOSYL)(THYMIN-1-YL)ALKANES AND THEIR INCORPORATION INTO OLIGODEOXYRIBONUCLEOTIDES. EFFECT OF NUCLEOBASE-SUGAR LINKER FLEXIBILITY ON THE FORMATION OF DNA-DNA AND DNA- RNA HYBRIDS

doi:10.1021/JO961548K

Paper

SYNTHESIS OF (2-DEOXY-ALPHA - AND -BETA -D-ERYTHRO-PENTOFURANOSYL)(THYMIN-1-YL)ALKANES AND THEIR INCORPORATION INTO OLIGODEOXYRIBONUCLEOTIDES. EFFECT OF NUCLEOBASE-SUGAR LINKER FLEXIBILITY ON THE FORMATION OF DNA-DNA AND DNA- RNA HYBRIDS

Published Nov 29, 1996 · J. Boal, A. Wilk, C. Scremin

Journal of Organic Chemistry

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Abstract

On the basis of modeling studies, the (2-deoxy-α- and β-d-erythro-pentofuranosyl) (thymin-1-yl) alkanes 1a,b and 2a,b were selected as potential conformational probes for altDNA oligonucleotides. A straightforward approach to the synthesis of 1a,b and 2a,b from commercial 2-deoxy-d-ribose (3) and 1-O-methyl-2-deoxy-3,5-di-O-p-toluoyl-d-erythro-pentofuranose (13), respectively, was developed. These nucleoside analogues were converted to the phosphoramidite derivatives 27a,b−30a,b and incorporated into oligonucleotide 31 at predetermined sites and defined internucleotidic motifs. The insertion of 1a,b according to either a (3‘ → 5‘)- or a (3‘ → 3‘)-internucleotidic polarity produced oligonucleotides exhibiting a slightly higher affinity for their complementary unmodified DNA sequence than for the corresponding RNA sequence (Table 3). Conversely, the incorporation of 2a into 31 according to a (3‘ → 3‘)-orientation generated, for the first time, an altDNA oligonucleotide displaying a greater affinity for its ...

Study Snapshot

The synthesis of (2-deoxy-- and -beta-d-erythro-pentofuranosyl) (thymin-1-yl) alkanes and their incorporation into oligodeoxyribonucleotides can lead to the formation of DNA-DNA

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

SYNTHESIS OF (2-DEOXY-ALPHA - AND -BETA -D-ERYTHRO-PENTOFURANOSYL)(THYMIN-1-YL)ALKANES AND THEIR INCORPORATION INTO OLIGODEOXYRIBONUCLEOTIDES. EFFECT OF NUCLEOBASE-SUGAR LINKER FLEXIBILITY ON THE FORMATION OF DNA-DNA AND DNA- RNA HYBRIDS

References

Citations

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Novel 1′-homo-N-2′-deoxy--nucleosides show potential as antiviral and cytotoxic compounds, offering potential for new nucleoside analogs and combinatorial chemistry.

The impact of an extended nucleobase-2′-deoxyribose linker in the biophysical and biological properties of oligonucleotides

The novel thymine derivative (T*) with an extended linker can be safely introduced at the 3′-end of siRNAs to generate potent inhibitors of gene expression by RNA interference.

Antifungal activity of 1'-homo-N-1,2,3-triazol-bicyclic carbonucleosides: A novel type of compound afforded by azide-enolate (3+2) cycloaddition.

Compounds 7a and 7b show promising antifungal activity against various fungi, including Candida spp.

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1′-homonucleosides and their analogues show potential as antiviral and anticancer drugs due to their structural flexibility and unique biological activity.

Stereocontrolled Synthesis of a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis of (+)-Aplysiallene Featuring a Stereospecific Ring Contraction.

This study successfully synthesized one of the possible stereoisomers of laurenidificin and formalized the total synthesis of (+)-aplysiallene using a stereospecific ring contraction strategy.

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Short-step anodic access to emissive RNA homonucleosides allows for the construction of useful libraries of synthetic probes with minimal structural perturbation and resistance to nonspecific degradation.

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This study presents a new method for synthesizing 1'-homo-N-nucleoside derivatives with anti-influenza activity, offering high conversion values and medium to high yields, without cytotoxic effects.

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