DNA catalyzed dithioacetalization in water

Abstract

The most popular hypothesis of precellular life is the "RNA World", which is utilizing RNA as both genetic as well as catalytic material. The chemical similarity between RNA and DNA leads researchers to investigate whether DNA has the catalytic function, although DNA is commonly viewed as a genetic carrier with a ubiquitous double-stranded architecture in living world. Nevertheless, the catalytic DNA has not been discovered in nature to date. In recent years, the catalytic function of DNA in nonbiological applications has aroused much interest to chemists in chemical synthesis such as DNA-templated organic synthesis and DNA-based asymmetric catalysis. However, the investigation of DNA as a direct catalyst for organic synthesis is largely elusive. Here we report that double-stranded DNA from herring sperm can catalyze the dithioacetalization in water for a wide range of aldehydes under mild reaction conditions. It is proposed that the phosphate groups of DNA together with the duplex architecture are responsible for the catalytic reaction. © 2013 Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences.