| Synthesis and properties of PNA oligomers containing orotic acid derivatives. | |
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MedLine Citation:
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PMID: 16248105 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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We have investigated the incorporation of C6-derivatives of uracil into polypyrimidine peptide nucleic acid oligomers (PNA). Starting with orotic acid (uracil-6-carboxylic acid) we have prepared a PNA monomer containing the methyl orotate nucleobase which is compatible with Fmoc-based synthesis. Treatment of the resin-bound oligomers with hydroxide or amines cleanly converted the ester to an orotic acid or orotamide-containing PNA. Alternatively, the methyl orotate-containing PNA was liberated from the resin by standard acidolysis. PNA bearing a modified nucleobase was found to hybridize to both poly(rA) and poly(dA). Complexes with poly(rA) were more stable than those with poly(dA) but both were destabilized relative to an unmodified PNA. Modification of a terminal residue was tolerated better than modification of an internal position. The type of charge provided by the modification affected the complex stability. In the worst case, an internal modification was nearly as detrimental as a base mismatch. |
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Authors:
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R H E Hudson; F Wojciechowski |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Nucleosides, nucleotides & nucleic acids Volume: 24 ISSN: 1525-7770 ISO Abbreviation: Nucleosides Nucleotides Nucleic Acids Publication Date: 2005 |
Date Detail:
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Created Date: 2005-10-26 Completed Date: 2005-12-15 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 100892832 Medline TA: Nucleosides Nucleotides Nucleic Acids Country: United States |
Other Details:
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Languages: eng Pagination: 1123-6 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Western Ontario, London, Ontario N6A 5B7, Canada. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Base Composition Base Pair Mismatch Models, Chemical Molecular Conformation Nucleic Acid Conformation Nucleic Acid Denaturation Oligodeoxyribonucleotides / chemistry Oligonucleotides / chemistry Orotic Acid / analogs & derivatives*, chemistry Peptide Nucleic Acids / chemical synthesis*, chemistry Poly A / chemistry Protein Structure, Tertiary Static Electricity |
| Chemical | |
Reg. No./Substance:
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0/Oligodeoxyribonucleotides; 0/Oligonucleotides; 0/Peptide Nucleic Acids; 24937-83-5/Poly A; 25191-20-2/poly(dA); 65-86-1/Orotic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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