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HOME > No.8, Feb 2017 > Research Highlights : Artificial enzyme for asymmetric synthesis using a synthetic chiral polymer

Artificial enzyme for asymmetric synthesis using a synthetic chiral polymer

By Shinichi Itsuno
Jun Miura (right of picture) with PhD candidate Bima Sena Bayu Dewantara
Professor Shinichi Itsuno (left) with one of his students

Cinchona alkaloid derivatives show catalytic activity in various kinds of asymmetric transformations in organic synthesis. These transformations are necessary steps in the production of pharmaceuticals. Shinichi Itsuno and his colleagues have successfully synthesized chiral polymers containing a cinchona alkaloid sulfonamide derivative as a repeating unit. This is the first example of a chiral polymer of cinchona sulfonamide, which shows high catalytic activity in the enantioselective desymmetrization of cyclic anhydrides.

Enzymes, high-molecular-weight chiral polymeric compounds, are complex biological catalysts. Capture of the substrate molecule, catalyzing the reaction, and release of the product are three important events performed by enzymes. In order to accomplish these events using a synthetic catalyst, the catalyst must necessarily have a large molecular weight so that it can act as a highly specific catalyst. To date no synthetic chiral polymers had been designed for this purpose, but now a research team from the Department of Environmental and Life Science at Toyohashi University of Technology has investigated a novel synthetic method for preparing chiral polymers containing repeating units of cinchona sulfonamide.

The lead author Shohei Takata said, "After testing many reaction conditions for the polymerization, we have synthesized chiral polymers containing cinchona sulfonamide repeating units. Chiral polymers are easily prepared according to the method we established."

"We have found that Mizoroki-Heck coupling was successful in synthesizing cinchona sulfonamide polymers," explains the leader of the research team, Professor Shinichi Itsuno, "Moreover, our chiral polymers showed high catalytic activity in asymmetric reactions.” Various kinds of such chiral polymers may be synthesized using this newly developed methodology to obtain various types of synthetic enzymes for specific reactions

Structure of cinchona sulfonamide polymer

Furthermore, the chiral polymers developed in this study are insoluble in the usual organic solvents or water. The insoluble polymeric catalysts can be packed into a column, into which the substrate compounds can be introduced. The desired product can then be continuously obtained from the column. Without a usual reaction vessel, a continuous flow system may be possible using the polymeric catalyst. The flow system is a necessary technology for the automation of fine chemical syntheses.

Funding agency: This work was partly supported by a Grant-in-Aid for Scientific Research on Innovative Areas “New Polymeric Materials Based on Element-Blocks (No.2401) and Scientific Research (C) JSPS KAKENHI Grant Number JP15H00732, JP15K05517.”


Shohei Takata, Yuta Endo, Mohammad Shahid Ullah, and Shinichi Itsuno (2016). Synthesis of cinchona alkaloid sulfonamide polymers as sustainable catalysts for the enantioselective desymmetrization of cyclic anhydrides, RSC Advances, 6 (76), 72300-72305. 10.1039/C6RA14535C







本研究は、文部科学省・日本学術振興会科研費(JP15H00732, JP15K05517)の補助を受けて行われました。

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Researcher Profile

Shinichi Itsuno
Name Shinichi Itsuno
Affiliation Department of Environmental and Life Sciences
Title Professor
Fields of Research Asymmetric reaction / Polymer-supported catalyst / Peptide folding