P666: Organic chemistry II research module: Synthesis of thiophene-arabinoside derivatives to Mycobacterium tuberculosis antigen 85C

Author: Treasure Sucheck, Mercy College of Ohio, USA

Co-Author: Cody Tyda, Nate Lewis, Bonnie Wonnel, Charlotte Reitz, Christy Woleslagel and Kayla VonSeggern, Mercy College, USA

Date: 8/5/14

Time: 5:15 PM6:30 PM

Room: LIB

Related Symposium: S33

Undergraduate research plays an important role in student learning along with motivating students to consider careers in chemistry and other STEM fields. At Mercy College we have introduced a research module to students in second semester organic chemistry that is centered on the synthesis of thiophene-arabinoside derivatives as potential inhibitors of Mycobacterium tuberculosis Antigen 85C. At the beginning of the course, students synthesize, purify and characterize two thiophenes using a standard procedure. Next, students search the literature and propose the synthesis of additional thiophenes. The proposed virtual thiophene-arabinosides are docked to Antigen 85C using Glide. Compounds with good docking scores are synthesized using the Gewald synthesis and conjugated to 5-thioarabinofuranoside. The resulting compounds are studied in follow up undergraduate research activities. Students present their work at the end of the semester at the Mercy College Research Symposium and are encouraged to present their work at regional conferences.