Development of novel gamma amino acid synthesis method using biomimetic hydrophobic hydration effect
- 자연과학대학
- Hit3064
- 2017-07-04
"Water enables an organic reaction that has never been possible"
The team found a groundbreaking synthesis method for synthesizing new gamma amino acid derivatives with an all-carbon quaternary stereogenic center. Gamma amino acids are widely used in various neurological and psychiatric diseases and are typical of pregabalin having a tertiary carbon chiral center of pajusa, a global pharmaceutical company for treating epilepsy, peripheral neuropathic pain and anxiety disorders. Therefore, the synthesis of novel gamma amino acid derivatives is a field of continuous research and efforts in the pharmaceutical industry in order to reduce side effects and improve drug efficacy. However, although gamma amino acids with quaternary carbon chiral centers are expected to have better pharmacological effects, they have not been able to overcome the synthetic difficulties and have been unable to develop related new drugs. As a result of the study, new gamma amino acid derivatives are expected to be available for the development of new drugs in the therapeutic drug.
According to the results of this study, hydrophobic hydration, which occurs when water is used as a reaction medium in the in vivo reaction, is precisely controlled using a hydrophobic organic catalyst. It has become possible to produce gamma amino acid derivatives having a quaternary carbon chiral center which could not be synthesized in the previous method. As a result of these studies, research on related drugs has become more active and the first steps toward the development of new drugs have been made. The results of this study were published in the February 2017 issue of 'Angewandte Chemie International Edition', a global scientific journal of chemistry, and it was named as a ‘hot paper’ in recognition of its importance.
* Title: "Water-Enabled Catalytic Asymmetric Michael Reactions of Unreactive Nitroaklenes: One-Pot Synthesis of Chiral GABA-Analogs with All-Carbon Quaternary Stereogenic Centers"
(1st author Shim, Jaehoon; Corresponding author: Song, Choongeui)