The 16th Hirata Award Winner
Department of Chemistry, Stanford University
Noncanonical membrane lipids as inspiration for synthesis and methods
Noah Z. Burns
Our group is particularly inspired by natural products not only because of their importance as synthetic targets but also due to their ability to serve as invaluable identifiers of unanswered methodological, biological, and biophysical questions. One major focus of our program has been the study of some of the most exotic membrane lipids ever discovered, representing a radical departure from the canonical hydrocarbons that dominate almost all prokaryotic and eukaryotic membranes. This includes highly unusual polycyclobutane-containing ladderane phospholipids from anammox bacteria and macrocyclic tetraether lipids containing up to 16 isolated methyl-bearing stereocenters from various archaea species. The former natural products have inspired recent work in our lab to develop new strategies for the practical and selective synthesis of different cyclobutane motifs. Total synthesis efforts towards archaeal lipids will also be discussed which have resulted in rapid and scalable routes that are enabling ongoing biophysical studies to better understand the properties and potential applications of these fascinating molecules.