Investigation of the effect of amino acid chirality in the internucleoside linker on DNA:DNA and DNA : RNA duplex stability
| Title | Investigation of the effect of amino acid chirality in the internucleoside linker on DNA:DNA and DNA : RNA duplex stability |
| Publication Type | Journal Article |
| Year of Publication | 2015 |
| Authors | Bagmare, S, Gunjal, AD, Kumar, VA |
| Journal | Tetrahedron |
| Volume | 71 |
| Issue | 16 |
| Pagination | 2442-2449 |
| Date Published | APR |
| Type of Article | Article |
| ISSN | 0040-4020 |
| Keywords | alpha-Amino acid, Chiral amide linkage, DNA, Five-atom amide linkage, L/D-Proline |
| Abstract | Enzymatically and chemically stable amide-linked di/oligonucleosides are highly desired synthetic targets in which the phosphodiester linkages in native DNA are replaced by amide linkers of appropriate length and stereochemistry. The five-atom amide-linked dimers, synthesized from 3'-amino-3'-deoxy thymidine, (alpha-(L/D) proline/prochiral glycine and thymidine/uridine-4'carboxylic acid derivatives, were incorporated into the DNA backbone to achieve partial replacement of selected phosphodiester linkages. The results stressed the importance of the chirality of linker amino acid. D-Proline was found to be the most compatible as an internucleoside linker in the DNA backbone to stabilize the complexes with DNA or RNA as compared to L-proline and glycine. (C) 2015 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2015.02.042 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.645 |