| Improved synthesis of oligonucleotides with an allylic backbone. Oligonucleotides containing acyclic, achiral nucleoside analogues: N-1 or N-9-[3-hydroxy-2-(hydroxymethyl)prop-1-enyl]nucleobases. | |
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MedLine Citation:
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PMID: 16525556 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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An improved phosphoramidite method is described to prepare oligonucleotides modified with the acyclic, achiral monomers 1. Examination of dimers, prepared on solid support or in solution, showed that phosphortriester dimers containing the allylic unit 1 were unstable towards bases, whereas phosphordiester dimers were stable. Phosphordiester dimers were obtained by replacing cyanoethyl phosphoramidites 2 with phosphoramidites 3, which gave phosphordiesters directly upon oxidation. The phosphordiester dimers were found to be stable towards capping and oxidation, but were somewhat labile towards acids. By reducing the contact time to acids during detritylation it was possible to prepare oligonucleotides containing 4 or 8 modified A, G or T units. The modified oligonucleotides hybridized to complementary DNA and RNA, although with reduced affinity (DeltaT(m) per modification -1 to -5 degrees C). |
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Authors:
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Britta M Dahl; Ulla Henriksen; Otto Dahl |
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Publication Detail:
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Type: Journal Article Date: 2006-01-25 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 4 ISSN: 1477-0520 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2006 Mar |
Date Detail:
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Created Date: 2006-03-09 Completed Date: 2007-09-24 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 1115-23 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100, Copenhagen, Denmark. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amides Base Sequence Chromatography, High Pressure Liquid Indicators and Reagents Magnetic Resonance Spectroscopy Models, Molecular Nucleic Acid Conformation Nucleosides / chemistry* Oligonucleotides / chemical synthesis*, isolation & purification Phosphonic Acids / chemistry* Phosphoric Acid Esters / chemistry* Phosphoric Acids Spectrometry, Mass, Fast Atom Bombardment |
| Chemical | |
Reg. No./Substance:
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0/Amides; 0/Indicators and Reagents; 0/Nucleosides; 0/Oligonucleotides; 0/Phosphonic Acids; 0/Phosphoric Acid Esters; 0/Phosphoric Acids; 13597-72-3/phosphoramide |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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