Hybridization Properties of a DeoxyoIigonucleotide Containing Four Formacetal Linkages
- 1 January 1991
- journal article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 10 (1-3), 231-234
- https://doi.org/10.1080/07328319108046449
Abstract
The deoxyoiigonucleotide “TCTCTCTCTCT” bearing four formacetal linkages has been synthesized. The hybridization properties of this compound with complementary RNA and single stranded DNA has been compared to control sequences bearing phosphodiester, phosphoramidate and methylphosphonate linkages. The formacetal oligomer hybridizes to RNA similarly to a diester and significantly better than the other neutral linkages. Recently we reported the synthesis of a deoxyoligonucleotide bearing two formacetal linkages at the three prime end (1). This oligomer was characterized for binding to a complementary RNA sequence. We now report the synthesis of the sequence 5′ TCTC*TC*TC*TCTTT where C is 5 methyl deoxycytidine and * is the formacetal linkage. Controls were prepared in which the modified linkage position * was the normal phosphodiester, methylphosphonate and methoxyethyl phosphoramidate. These four sequences which differ only in the backbone linkage at the starred positions were compared for their ability to hybridize to a complementary RNA and single stranded DNA sequences.Keywords
This publication has 10 references indexed in Scilit:
- Deoxyoligonucleotide analogs based on formacetal linkagesTetrahedron Letters, 1990
- Oligodeoxynucleoside phosphoramidates and phosphorothioates as inhibitors of human immunodeficiency virus.Proceedings of the National Academy of Sciences, 1988
- Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkagesNucleic Acids Research, 1987
- Oligoribonucleotide synthesis using T7 RNA polymerase and synthetic DNA templatesNucleic Acids Research, 1987
- Deoxynucleoside H-Phosphonate diester intermediates in the synthesis of internucleotide phosphate analoguesTetrahedron Letters, 1986
- Solid-phase synthesis of oligodeoxyribonucleoside methylphosphonatesBiochemistry, 1986
- Synthesis of DNA via deoxynudeoside H-phosphonate IntermediatesNucleic Acids Research, 1986
- Biochemical and biological effects of nonionic nucleic acid methylphosphonatesBiochemistry, 1981
- Selective inhibition of Escherichia coli protein synthesis and growth by nonionic oligonucleotides complementary to the 3′ end of 16S rRNAProceedings of the National Academy of Sciences, 1981
- Synthesis and enzymatic properties of deoxyribooligonucleotides containing methyl and phenylphosphonate linkagesNucleic Acids Research, 1979