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High-quality oligo-RNA synthesis using the new 2′-O-TEM protecting group by selectively quenching the addition of p-tolyl vinyl sulphone to exocyclic amino functions
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Bioorganic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Bioorganic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Bioorganic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Bioorganic Chemistry.
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2007 (English)In: Canadian journal of chemistry (Print), ISSN 0008-4042, E-ISSN 1480-3291, Vol. 85, no 4, 293-301 p.Article in journal (Refereed) Published
Abstract [en]

During the F--promoted deprotection of the oligo-RNA, synthesized using our 2′-O-(4-tolylsulfonyl)ethoxymethyl (2′-O-TEM) group [Org. Biomol. Chem. 5, 333 (2007)], p-tolyl vinyl sulphone (TVS) is formed as a by-product. The TVS formed has been shown to react with the exocyclic amino functions of adenosine (A), guanosine (G), and cytidine (C) of the fully deprotected oligo-RNA to give undesirable adducts, which are then purified by HPLC and unambiguously characterized by 1H, 13C Heteronuclear Multiple Bond Correlation (HMBC) NMR and mass spectroscopic analysis. The relative nucleophilic reactivities of the nucleobases toward TVS have been found to be the following: N6-A > N4-C > N2-G > > N3-U. This reactivity of TVS toward RNA nucleobases to give various Michael adducts could, however, be suppressed by using various amines as scavengers. Among all these amines, morpholine and piperidine are the most efficient scavenger for TVS, which gave highly pure oligo-RNA even in the crude form and can be used directly in RNA chemical biology studies.

Place, publisher, year, edition, pages
2007. Vol. 85, no 4, 293-301 p.
Keyword [en]
RNA synthesis, RNA alkylation, p-tolyl vinyl sulphone, Michael addition
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:uu:diva-13163DOI: 10.1139/V07-025ISI: 000246576200008OAI: oai:DiVA.org:uu-13163DiVA: diva2:40933
Available from: 2008-04-15 Created: 2008-04-15 Last updated: 2017-12-11Bibliographically approved
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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Supervisors
Available from: 2010-03-10 Created: 2010-02-02 Last updated: 2010-03-11

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Zhou, ChuanzhengHoncharenko, DmytroChattopadhyaya, Jyoti

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