| Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons. | |
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MedLine Citation:
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PMID: 8668548 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Boron-modified nucleic acids comprise a new set of DNA mimics that have potential biological and therapeutic applications. A series of nine dinucleotides containing N7-cyanoborane-2'-deoxyguanosine ((7b)dG) at the 3', 5' or both positions of the phosphodiester linkage have been synthesized using solution phase phosphoramidite chemistry. Fmoc was used as the 5'-protecting group because of incompatibility of the cyanoborane moiety with 5'-DMT cations generated during the deprotection step. The presence of the cyanoborane group was confirmed on the basis of Fab-MS and 1H NMR spectroscopy. The H-8 proton of (7b)dG in the dinucleotides shifted 0.35-0.80 p.p.m. downfield relative to that of unmodified dG. A comparison of the D20 exchange kinetics of the H-8 proton at 60 degrees C showed that H-8 of (7b)dG is very labile relative to unmodified dG, indicating that the N7-cyanoborane modification increases the acidity of the H-8 proton of (7b)dG. These studies illustrate the feasibility of synthesizing boron-containing oligonucleotides which are modified at the N7-guanine to block Hoogsteen pairing in the DNA major groove. |
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Authors:
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A Hasan; H Li; J Tomasz; B R Shaw |
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Publication Detail:
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Type: Comparative Study; Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Nucleic acids research Volume: 24 ISSN: 0305-1048 ISO Abbreviation: Nucleic Acids Res. Publication Date: 1996 Jun |
Date Detail:
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Created Date: 1996-08-05 Completed Date: 1996-08-05 Revised Date: 2009-11-18 |
Medline Journal Info:
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Nlm Unique ID: 0411011 Medline TA: Nucleic Acids Res Country: ENGLAND |
Other Details:
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Languages: eng Pagination: 2150-7 Citation Subset: IM |
Affiliation:
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Department of Chemistry, P.M. Gross Chemical Laboratory, Duke University, Durham, NC 27708-0346, USA. |
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| MeSH Terms | |
Descriptor/Qualifier:
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Amides
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chemistry Boron / chemistry* Boron Compounds / chemistry* DNA / chemistry* Deoxyguanosine / analogs & derivatives*, chemistry Deuterium Fluorenes Hydrogen-Ion Concentration Kinetics Magnetic Resonance Spectroscopy Nucleotides / chemical synthesis, chemistry* Phosphoric Acids / chemistry Protons* Spectrometry, Mass, Fast Atom Bombardment |
| Grant Support | |
ID/Acronym/Agency:
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5UO1-CA60139/CA/NCI NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Amides; 0/Boron Compounds; 0/Fluorenes; 0/Nucleotides; 0/Phosphoric Acids; 0/Protons; 2817-45-0/phosphoramidic acid; 7440-42-8/Boron; 7782-39-0/Deuterium; 9007-49-2/DNA; 961-07-9/Deoxyguanosine |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
| Full Text | |
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Journal Information Journal ID (nlm-ta): Nucleic Acids Res ISSN: 0305-1048 ISSN: 1362-4962 |
Article Information Download PDF  Print publication date: Day: 1 Month: 6 Year: 1996 Volume: 24 Issue: 11 First Page: 2150 Last Page: 2157 ID: 145900 PubMed Id: 8668548 Publisher Item Identifier: 6b0012 |
| Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons. | |
| A Hasan | |
| H Li | |
| J Tomasz | |
| B R Shaw | |
| Department of Chemistry, P.M. Gross Chemical Laboratory, Duke University, Durham, NC 27708-0346, USA. |
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