121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-321
Subject First Structural Revision of Baulamycin A and Structure-Activity Relationships of Baulamycin A Derivatives
Authors Sandip Sengupta, Hak Joong Kim1, Injae Shin2, Taebo Sim3,*
chemical kinomics, postdoc, Korea
1Department of Chemistry, Korea University, Korea
2Korea University, Korea
3Chemical Kinomics Research Center, Korea Institute of Science and Technology, Korea
Abstract Total synthesis of the proposed structure of baulamycin A was performed. The spectral properties of the synthetic compound differ from those reported for the natural product. On the basis of NMR study, we proposed two other possible structures for natural baulamycin A. Total syntheses of these two substances were performed, which enabled assignment of the correct structure of baulamycin A. Key features of the convergent and fully stereo-controlled route include Evans Aldol1 and Brown allylation2 reactions to construct the left fragment, a prolinol amide-derived alkylation/desymmetrization to install the methyl substituted centers in the right fragment, and finally a Carreira alkynylation3 to join both fragments. In addition, we have determined the inhibitory activities against the enzyme SbnE4 of novel baulamycin A derivatives. This SAR study provides useful insight into the design of novel SbnE inhibitors that overcome the drug resistance of pathogens, which cause life-threatening infections.
E-mail sengsandip@yahoo.com