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Title

DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems

AuthorsHäring, Marleen; Pérez-Madrigal, Maria M.; Kühbeck, Dennis; Pettignano, Asja; Quignard, Françoise
KeywordsBuffer solutions
DNA
C-C bond formation
Henry reaction
Nitroaldol reaction
Issue Date1-Mar-2015
PublisherMultidisciplinary Digital Publishing Institute
CitationMolecules
AbstractIn this manuscript we report a critical evaluation of the ability of natural DNA to mediate the nitroaldol (Henry) reaction at physiological temperature in pure water. Under these conditions, no background reaction took place (i.e., control experiment without DNA). Both heteroaromatic aldehydes (e.g., 2-pyridinecarboxaldehyde) and aromatic aldehydes bearing strong or moderate electron-withdrawing groups reacted satisfactorily with nitromethane obeying first order kinetics and affording the corresponding β-nitroalcohols in good yields within 24 h. In contrast, aliphatic aldehydes and aromatic aldehydes having electron-donating groups either did not react or were poorly converted. Moreover, we discovered that a number of metal-free organic buffers efficiently promote the Henry reaction when they were used as reaction media without adding external catalysts. This constitutes an important observation because the influence of organic buffers in chemical processes has been traditionally underestimated
Publisher version (URL)http://dx.doi.org/10.1155/2013/631875/10.3390/molecules20034136
URIhttp://hdl.handle.net/10261/130258
DOIhttp://dx.doi.org/10.3390/molecules20034136
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