| The kinetics and mechanism of the acid-catalysed detritylation of nucleotides in non-aqueous solution. | |
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MedLine Citation:
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PMID: 19081945 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The kinetics and mechanism of the deprotection (detritylation) of 5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidine nucleoside catalysed by dichloroacetic acid to give a 4,4'-dimethoxytrityl carbocation have been studied in toluene, dichloromethane and acetonitrile. There is little or no effect of solvent polarity on the equilibrium and rate constants. Entropies of activation are highly negative approximately -105 J K(-1) mol(-1) and similarly show little variation with solvent. Addition of small amounts of water to the reaction medium reduces the detritylation rate, presumably through its effect on the solution acidity. All observations are compatible with detritylation occurring through a concerted general acid-catalysed mechanism rather than a stepwise A1 process. |
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Authors:
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Mark A Russell; Andrew P Laws; John H Atherton; Michael I Page |
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Publication Detail:
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Type: Journal Article Date: 2008-11-06 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 7 ISSN: 1477-0539 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2009 Jan |
Date Detail:
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Created Date: 2008-12-16 Completed Date: 2009-04-24 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: 52-7 Citation Subset: IM |
Affiliation:
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Department of Chemical and Biological Sciences, University of Huddersfield, Queensgate, Huddersfield, UK HD1 3DH. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acids
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chemistry Alcohols / chemistry Catalysis Dichloroacetate / chemistry Dose-Response Relationship, Drug Entropy Kinetics Magnetic Resonance Spectroscopy Models, Chemical Molecular Structure Nucleotides / chemistry* Solutions Solvents / chemistry Temperature Water / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Acids; 0/Alcohols; 0/Nucleotides; 0/Solutions; 0/Solvents; 13425-80-4/Dichloroacetate; 7732-18-5/Water |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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