Phosphoramidate analogues of DNA: synthesis and thermal stability of heteroduplexes
- 10 June 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 16 (11) , 4831-4839
- https://doi.org/10.1093/nar/16.11.4831
Abstract
The deoxyoligonucleotide 5′ AATCGGGCATGGATT (15-mer) was synthesized containing 12 phosphoramidate linkages derived from 2 primary and 2 secondary amines. The oligonucleotides were purified by reverse phase HPLC and characterized by PAGE. The thermal stability of the duplexes derived from these compounds, when hybridized to the complementary diester linked oligomer, were determined and compared to the diester and methanephosphonate oligomer. The results indicated that all analogue oligomers form less stable duplexes then the diester oligomer. A large difference was observed between primary and secondary amine derived phosphoramidates.Keywords
This publication has 14 references indexed in Scilit:
- Phosphorothioate analogs of oligodeoxynucleotides: inhibitors of replication and cytopathic effects of human immunodeficiency virus.Proceedings of the National Academy of Sciences, 1987
- Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkagesNucleic Acids Research, 1987
- Solid-phase synthesis of oligodeoxyribonucleoside methylphosphonatesBiochemistry, 1986
- Synthesis of DNA via deoxynudeoside H-phosphonate IntermediatesNucleic Acids Research, 1986
- Effects of pendant groups at phosphorus on binding properties of d-ApA analoguesNucleic Acids Research, 1986
- Complementary Oligonucleotide Probe of Vesicular Stomatitus Virus Matrix Protein mRNA TranslationBiophysical Journal, 1986
- Characterization of sequence-specific oligodeoxyribonucleoside methylphosphonates and their interaction with rabbit globin mRNABiochemistry, 1985
- Oligothymidylate analogues having stereoregular, alternating methylphosphonate/phosphodiester backbones. Synthesis and physical studies.Journal of Biological Chemistry, 1980
- Nonionic nucleic acid analogs. Synthesis and characterization of dideoxyribonucleoside methylphosphonatesBiochemistry, 1979
- Transfer ribonucleic acids and related compounds. I. Synthesis of ribooligonucleotides using aromatic phosphoramidates as a protecting groupJournal of the American Chemical Society, 1970