Prof. Scott Taylor wins the Bernard Belleau Award for contributions to medicinal chemistry

Friday, March 24, 2023
Scott Taylor

Dr. Scott Taylor has been awarded the Bernard Belleau Award from the Chemical Institute of Canada for his numerous and important contributions to medicinal chemistry. Taylor is a world leader in the study of an important class of antibacterial drugs known as the calcium-dependent lipopeptide antibiotics (CDAs).

The Bernard Belleau Award is given to a scientist who has made a distinguished contribution to the field of medicinal chemistry through research involving biochemical or organic chemical mechanisms.

Taylor's expertise is in organic synthesis. His research often involves the development of new methodology and molecules. He uses these new molecules as research tools to investigate organic chemical and/or biochemical mechanisms and develop inhibitors with therapeutic potential.

One of the most notable accomplishments is Taylor's contribution to the understanding of the clinically used antibiotic daptomycin. Daptomycin (Cubicin) is a lipopeptide antibiotic used in the treatment of systemic and life-threatening infections caused by Gram-positive organisms. The antibiotic was introduced in the early 2000s, but the mechanism by which it specifically targets and kills bacterial cells remained vague.

Over the past 10 years, Taylor's contributions to the total synthesis of daptomycin and its analogues have enabled groundbreaking studies that have greatly expanded the understanding of daptomycin’s mechanism of action.

In 2015, Taylor and his team determined the solid phase total synthesis of daptomycin. To this day, it is the most elegant and flexible route devised for the synthesis of this clinically important antibiotic. This synthetic route also enabled Taylor and his team to prepare structural analogues of daptomycin that were key to establishing that the antibiotic operates by forming oligomeric, cation-selective pores in bacterial cell membranes.

Recently, Taylor improved the synthesis of daptomycin by developing a synthetic strategy that uses Fmoc building blocks exclusively. The key to this accomplishment was his astute analysis of the problems that had foiled earlier attempts using Fmoc-only synthesis. Taylor deduced that the initially observed very low yield was the result of a side reaction and by making a minor modification, Taylor and his team were able to increase the yield of daptomycin to 22 per cent. This work has opened the door to the synthesis of many daptomycin analogs, which could lead to the development of new antibiotics for active bacteria with resistance to other antibiotics.

In addition to his work on daptomycin, Taylor has also published the first total syntheses of a number of other structurally complex natural products including the lipopeptide antibiotics paenibacterin, A54145 and CDA.

Taylor is the second Waterloo chemist to win this award, Dr. John Honek won the award in 2014.

Taylor will give a lecture when receives the award at the Canadian Chemistry Conference and Exhibition in Vancouver, British Columbia this June.

Congratulations, Dr. Taylor!