Kwasy nukleinowe jako katalizatory reakcji chemicznych
Journal Title: Wiadomości Chemiczne - Year 2012, Vol 66, Issue 1
Abstract
Nucleic acids, due to their specific structure, are effective and durable carriers of genetic information. They have also been used as catalysts in chemical reactions. The right-handed DNA double helix structure has become one of the icons of modern science, and its share in asymmetric catalysis is undeniable. In these reactions, DNA is a source of chirality and proximity between oligonucleotides and complexes of copper during catalysis, what allows a direct transfer of chirality from DNA to the reaction product. Almost complete regioselectivity and excellent enantioselectivity of the aforementioned reactions in water are the evidence of the potential of asymmetry based on DNA. Asymmetric catalysis used in organic synthesis, allows achieving high enantioselectivity. This strategy has been successfully used to create new C-C bonds in Diels- Alder cycloaddition, Friedel-Crafts alkylation and Michael addition using copper complexes with oligonucleotides as catalysts. The important factor to optimize the reaction of asymmetric catalysis in the presence of DNA constitutes its sequence. It has been shown that the use of the double helix DNA can provide the product with higher enantiomeric excess than using the single strand of DNA. In addition, the results of the study suggest that Friedel-Crafts alkylation is accelerated by DNA almost 30-fold. The same correlation is observed in Diels-Alder cycloaddition. Due to promising results, further testing directed at the possibility of using catalytic DNA is being conducted.
Authors and Affiliations
Małgorzata Bukowiecka-Matusiak, Marta Sobczak
Keywords
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