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Synthesis and Structure of New Methylene-bridged hexopyranosyl nucleoside (BHNA)
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Bioorganic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Bioorganic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Bioorganic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Bioorganic Chemistry.
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2009 (English)In: Heterocycles, ISSN 0385-5414, E-ISSN 1881-0942, Vol. 78, no 7, 1715-1728 p.Article in journal (Refereed) Published
Abstract [en]

A new member of hexopyranosyl nucleoside family, methylene-bridged   hexopyranosyl nucleoside (BHNA), has been synthesized through   generation of carbon radical at C6' in [6'S-Me, 7'S-Me]-carba-LNA T  nucleoside, followed by rearrangement to C4' radical which was quenched   by hydrogen atom to give BHNA. The stereoelectronic requirement for   this unusual radical rearrangement has been elucidated by chemical   model building and ab intio calculations to show that the coplanarity of the single electron occupied p-orbital at C6' with sigma*(O4'-C4')   plays an important role for the rearrangement reaction to take place.   The solution structure of BHNA has also been studied using NMR as well   as by ab initio calculations. The new six-membered pyranosyl ring in  BHNA, unlike other known hexopyranosyl nucleosides, adopts a twist   conformation, with base moiety occupying the axial position while  3'-hydroxymethyl and 4'-hydroxyl occupying the equatorial position.

Place, publisher, year, edition, pages
2009. Vol. 78, no 7, 1715-1728 p.
Keyword [en]
Conformationally Constrained Nucleoside, Hexopyranosyl Nucleoside, Radical Rearrangement, Conformational Analysis, ab initio Calculation
National Category
Biological Sciences
Identifiers
URN: urn:nbn:se:uu:diva-106720DOI: 10.3987/COM-09-11660ISI: 000268441500003OAI: oai:DiVA.org:uu-106720DiVA: diva2:225940
Available from: 2009-06-29 Created: 2009-06-29 Last updated: 2017-12-13
In thesis
1. Conformationally Constrained Nucleic Acids as Potential RNA Targeting Therapeutics
Open this publication in new window or tab >>Conformationally Constrained Nucleic Acids as Potential RNA Targeting Therapeutics
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
Publisher
67 p.
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Bioorganic Chemistry
Identifiers
urn:nbn:se:uu:diva-113680 (URN)
Public defence
2010-03-31, C10:301, BMC, Husargatan 3, Uppsala, 14:00 (English)
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Available from: 2010-03-10 Created: 2010-02-02 Last updated: 2010-03-11

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Plashkevych, Oleksandr

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