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SUMMARY:New Strategies for Stereoselective Radical Biocatalysis
LOCATION:Chemistry A101
TZID:America/Denver
DTSTART:20250224T160000
UID:2026-04-20-11-16-13@natsci.colostate.edu
DTSTAMP:20260420T111613
Description:About the Seminar:\n\nRadical reactions have enjoyed widespread
  applications in both small molecule and macromolecule synthesis. However\
 , it remains challenging to control the stereochemistry of radical transfo
 rmations and to discover novel modes of radical catalysis which are not kn
 own in either organic chemistry or biochemistry. Combining synthetic chemi
 stry\, enzymology and protein engineering\, our group advanced two new bio
 catalytic strategies for stereoselective free radical processes. First\, b
 y capitalizing on the innate redox properties of first-row transition-meta
 l cofactors\, we repurposed and evolved natural metalloproteins to catalyz
 e unnatural radical reactions in a stereocontrolled fashion. Through a met
 alloenzyme-catalyzed halogen atom transfer mechanism (XAT\, X = F\, Cl\, B
 r and I)\, a range of radical C–C\, C–Br\, and C–F bond forming reac
 tions proceeded with excellent total turnover numbers (up to 20\,000) and 
 outstanding stereocontrol. Second\, by merging visible light photoredox ca
 talysis and biocatalysis\, we advanced a novel mode of pyridoxal radical b
 iocatalysis which is new to both chemistry and biology. Synergistic photob
 iocatalysis allowed us to repurpose structurally and functionally diverse 
 pyridoxal phosphate (PLP)-dependent enzymes as radical enzymes\, leading t
 o novel radical PLP enzymology. Pyridoxal radical biocatalysis provides co
 nvergent\, stereoselective\, and protecting-group-free access to a range o
 f useful non-canonical amino acids\, including those bearing a stereochemi
 cal triad and/or tetrasubstituted stereocenters which remained difficult t
 o prepare by other chemical and biocatalytic means. Furthermore\, we demon
 strate that the exploitation of biocatalyst-photocatalyst synergy affords 
 a new paradigm to design and develop stereoselective intermolecular radica
 l reactions with synthetic utility.\n\nAbout the Speaker: \n\nDr. Yang re
 ceived his Ph.D. degree in Organic Chemistry in 2016 under the guidance of
  Prof. Steve Buchwald at MIT. In the Buchwald lab\, he developed CuH-catal
 yzed methods for the asymmetric hydrofunctionalization of simple olefins. 
 As an NIH Postdoctoral Fellow working with Prof. Frances Arnold at Caltech
 \, Dr. Yang studied biocatalysis and protein engineering and developed bio
 catalytic asymmetric C–H amination. Dr. Yang started his independent car
 eer in the Department of Chemistry and Biochemistry at the University of C
 alifornia Santa Barbara in 2020. By integrating synthetic chemistry\, bioc
 atalysis\, protein engineering and computational tools\, the Yang group is
  reprograming nature’s biosynthetic machineries to address challenging p
 roblems in synthesis\, catalysis and biomolecular engineering. The Yang gr
 oup recently coined and implemented two new strategies to advance novel st
 ereoselective biocatalytic reactions\, including metalloredox radical bioc
 atalysis and pyridoxal radical biocatalysis. Dr. Yang is a recipient of th
 e Regent’s Junior Faculty Fellowship Award (2021)\, Faculty Career Devel
 opment Award (2022)\, National Science Foundation (NSF) CAREER Award (2022
 )\, National Institutes of Health (NIH) Maximizing Investigators\\' Resear
 ch Award (2022)\, Thieme Chemistry Journals Award (2023)\, Army Research O
 ffice (ARO) Young Investigator Award (2023)\, Packard Fellowship (2023)\, 
 Sloan Research Fellowship (2024)\, Department of Energy (DOE) Early Career
  Award (2024)\, Amgen Young Investigator Award (2024) and Novartis Early C
 areer Award (2025). 4:00 pm
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