Haering, Marleen and Perez-Madrigal, Maria M. and Kuehbeck, Dennis and Pettignano, Asja and Quignard, Francoise and Diaz Diaz, David (2015) DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems. MOLECULES, 20 (3). pp. 4136-4147. ISSN 1420-3049,
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In 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 beta-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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C BOND FORMATION; HYDROXYNITRILE LYASE; GELATIN; ACID; RNA; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. David Díaz Díaz |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 24 Jul 2019 11:16 |
| Last Modified: | 24 Jul 2019 11:17 |
| URI: | https://pred.uni-regensburg.de/id/eprint/5872 |
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