Duplex and triplex formation of mixed pyrimidine oligonucleotides with stacking of phenyl-triazole moieties in the major groove
| Autor: | Holger Døssing, Frank Jensen, Birte Vester, Poul Nielsen, Nicolai K. Andersen |
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| Rok vydání: | 2011 |
| Předmět: |
Models
Molecular DNA Complementary Pyrimidine Stereochemistry Stacking Triazole Oligonucleotides Deoxycytidine RNA Complementary chemistry.chemical_compound Nucleotide chemistry.chemical_classification Base Sequence Molecular Structure Chemistry Oligonucleotide Nucleotides Circular Dichroism Organic Chemistry Cytidine Nucleosides Triazoles Deoxyuridine Uridine Pyrimidines Duplex (building) Nucleic Acid Conformation |
| Zdroj: | Andersen, N K, Døssing, H, Jensen, F, Vester, B & Nielsen, P 2011, ' Duplex and Triplex Formation of Mixed Pyrimidine Oligonucleotides with Stacking of Phenyl-triazole Moieties in the Major Groove ', Journal of Organic Chemistry, vol. 76, no. 15, pp. 6177-87 . https://doi.org/10.1021/jo200919y Andersen, N K, Døssing, H B, Jensen, F, Vester, B & Nielsen, P 2011, ' Duplex and triplex formation of mixed pyrimidine oligonucleotides with stacking of phenyl-triazole moieties in the major groove ', Journal of Organic Chemistry, vol. 76, no. 15, pp. 6177-87 . https://doi.org/10.1021/jo200919y |
| ISSN: | 1520-6904 |
| Popis: | 5-(1-Phenyl-1,2,3-triazol-4-yl)-2′-deoxycytidine was synthesized from a modified CuAAC protocol and incorporated into mixed pyrimidine oligonucleotide sequences together with the corresponding 5-(1-phenyl-1,2,3-triazol-4-yl)-2′-deoxyuridine. With consecutive incorporations of the two modified nucleosides, improved duplex formation with a complementary RNA and improved triplex formation with a complementary DNA duplex were observed. The improvement is due to π–π stacking of the phenyl-triazole moieties in the major groove. The strongest stacking and most pronounced positive influence on thermal stability was found in between the uridine analogues or with the cytidine analogue placed in the 3′ direction to the uridine analogue. Modeling indicated a different orientation of the phenyl-triazole moieties in the major groove to account for the difference between the two nucleotides. The modified oligonucleotides were all found to be significantly stabilized toward nucleolytic degration. |
| Databáze: | OpenAIRE |
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