Chemistry Weekly Seminar - Doug Fansher, PhD Candidate

Title

Developing the Promiscuous Aldolase NahE for Applications in Biocatalysis

Abstract

Enzymes are responsible for a wide variety of chemical reactions within the natural world. Often these enzymes have the benefit of being able to catalyze reactions under mild conditions with a high degree of stereoselectivity and enantioselectivity that is sometimes difficult to achieve with traditional synthesis. The type 1 aldolase family has attracted attention as a biocatalyst in recent years, but most family members have limited substrates scopes. However, we have shown that a member of the NAL-subfamily, NahE, can accept over 40 aldehyde substrates forming α,β-unsaturated-2-keto acids in near quantitative yields. Furthermore, by using a β-aminoaldehyde, we can exploit the enzymatic mechanism and form 2-quinaldic acids in up to 92% yield. To our knowledge, this is the first reported use of a biocatalysis to form quinolines. We have also shown that NahE is able to accept electrophiles other than aldehydes to further expand the synthetic utility of the NahE as a biocatalyst.

Date:          Thursday, April 1, 2021

Time:         1:30 p.m.

Zoom link available by request from chem.dept@usask.ca