Chemical Society Seminar: Professor Konrad Tiefenbacher - Terpene Biosynthesis as Inspiration for Supramolecular Catalysis

Event

Maass Chemistry Building Room 10, 801 rue Sherbrooke Ouest, Montreal, QC, H3A 0B8, CA

Nature’s extraordinary elegance when performing chemical reactions has fascinated and inspired chemists for decades. Arguably, one of the most complex organic transformations performed in living organisms, is the tail-to-head terpene (THT) cyclization.[1,2] It allows the construction of the most diverse class of natural products, namely terpenes, via nature’s way of combinatorial chemical synthesis. Thousands of different natural products are formed from just a handful of simple, acyclic starting materials: geranyl pyrophosphate (monoterpenes), farnesyl-PP (sesquiterpenes) and geranylgeranyl-PP (diterpenes). Nature utilizes enzymes, termed cyclases or terpene synthases, to carry out this complex transformation. Building upon our initial results,[3,4,5] we explore possibilities to utilize supramolecular structures to mimic such complex transformations in the laboratory. The latest results in this direction will be presented.

[1]     S. V. Pronin, R. A. Shenvi Nature Chem. 2012, 4, 915. [2]      D. J. Miller, R. K. Allemann Nat. Prod. Rep. 2012, 29, 60. [3] Q. Zhang, K. Tiefenbacher J. Am. Chem. Soc. 2013, 135, 16213. [4] Q. Zhang, K. Tiefenbacher Nature Chem. 2015, 7, 197. [5] Q. Zhang, L. Catti, J. Pleiss, K. Tiefenbacher J. Am. Chem. Soc. 2017, 139, 11482.

Contact Information

Contact: 
Jim Gleason
Email: 
jim.gleason [at] mcgill.ca