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A Report on G-Quadruplex DNA-Based Enantioselective Catalysis
  English.dicp.cas.cn    Posted:2012-08-31

The research team led by Prof. Can Li at the State Key Laboratory of Catalysis of Dalian Institute of Chemical Physics, CAS, reported that human telomeric G-quadruplex DNA (ht-G4DNA) shows enantioselective catalytic functions in the Diels−Alder reaction and Friedel−Crafts reaction. [Angew. Chem. Int. Ed. (DOI: 10.1002/anie.201204850) and Chem. Commun. (DOI: 10.1039/C2CC31320K)].

DNA is known as genetic materials of living organisms, generally existing in duplex structures in nature. Normally, DNA has not been regarded as a catalytic species so far, owing to its stable double-stranded scaffold. However, once the single-stranded DNA is dissociated from its complementary partner strand, it could form a chemically active tertiary structure such as G4DNA. Li and his colleagues have found that ht-G4DNA alone can catalyze the Diels−Alder reaction and Friedel−Crafts reaction enantioselectively. When an artificial G4DNA metalloenzyme was assembled from G4DNA and Cu2+ ions, the reactivity and enantioselectivity of the reactions were significantly enhanced. Furthermore, it was found that the configuration of the enantiomer was sensitive to the conformation of the G4DNA. For the Diels−Alder reaction, the absolute configuration of the Diels−Alder products could even be reversed when the conformation of the G4DNA was switched from antiparallel to parallel. In addition, both the reaction rate and the enantioselectivity of the Diels–Alder reaction were found to be dependent on the DNA sequence.

Natural biological catalysts usually consist of protein enzymes and RNA enzymes, whereas DNA is considered solely as a genetic material. Breaker and Joyce reported in 1994 that an artificial deoxyribozyme can catalyze the cleavage of a single ribonucleotide. Recently, a DNA-based catalyst composed of double-stranded DNA and metal complex has been found to be active for several asymmetric reactions. However, whether it is the DNA itself that exerts the enantioselective catalytic function is still an open question. In this research, they have observed that ht-G4DNA showed an enantioselective catalytic function. This could provide an inspiration in exploring the catalytic function of DNA.

This work was financially supported by the National Natural Science Foundation of China.

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