Study On The Synthesis And Polymerization Of Enediyne Compounds Containing Chiral Amino Acid Moieties

It was found that natural occurring enediyne compounds exhibited great values in anti-bacteria and anti-tumor fields early in1980s. These enediyne compounds could form diradicals through Bergman cyclization, with which to kill bacteria and tumor cells by cleaving their DNA chains. This discovery made the enediyne compounds and Bergman cyclization reaction as hot research topics. Bergman cyclization is a cyclization reaction forming diradical intermediates, when enediyne compounds are under heating or ultraviolet irradiation conditions. Bergman cyclization reaction has great application prospect not only in the medicine field, but also in polymer field. However, there were a few studies on preparation of chiral polymers through Bergman cyclization.Chiral polymers are widely present in the natural polymers, such as nucleic acids, proteins, polysaccharides. The unique properties of these chiral polymers have attracted widespread attentions from the scientific community in the field of life sciences. The rapid development of the synthesis of chiral compounds, not only overcomes the defects of the natural chiral compounds in a widespread applications, but also expands the research scope of the chiral compounds, making the structure of chiral polymer more well-controlled.In order to study the application value of Bergman cyclization on the synthesis of chiral polymers, a series of enediyne compounds with a chiral centers and different amino groups were synthesized in this research. These chiral enediynes polymerized into chiral polymers via thermal-triggered or photo-induced Bergman cyclization.The enediyne compounds and as-prepared chiral polymer were characterized by Differential Scanning Calorimetry (DSC), Fourier Transform Infrared Spectroscopy (FTIR), Gel Permeation Chromatography (GPC), Circular Dichroism (CD).Results showed that chiral polymers were synthesized by the thermal-triggered or light-induced Bergman cyclization of the as-prepared enediyne compounds with a chiral centers an d different amino groups.