Cited by 254Enzyme Catalysis and ImmobilizationRadical Photochemical ReactionsAsymmetric Synthesis and Catalysis

Stereoselective amino acid synthesis by synergistic photoredox-pyridoxal radical biocatalysis

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Cheng, Lei, Li, Dian, Mai, Binh Khanh, Bo, Zhiyu, Cheng, Lida, Liu, Peng, Yang, Yang·2023·Science

Abstract

Developing synthetically useful enzymatic reactions that are not known in biochemistry and organic chemistry is an important challenge in biocatalysis. Through the synergistic merger of photoredox catalysis and pyridoxal 5′-phosphate (PLP) biocatalysis, we developed a pyridoxal radical biocatalysis approach to prepare valuable noncanonical amino acids, including those bearing a stereochemical dyad or triad, without the need for protecting groups. Using engineered PLP enzymes, either enantiomeric product could be produced in a biocatalyst-controlled fashion. Synergistic photoredox - pyridoxal radical biocatalysis represents a powerful platform with which to discover previously unknown catalytic reactions and to tame radical intermediates for asymmetric catalysis.

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Cited by

Sorted by citations

Authors
Cheng, L., Li, D., Mai, B. K., Bo, Z., Cheng, L., Liu, P., & Yang, Y.
Affiliations
  • University of California, Santa Barbara (US)
  • University of Pittsburgh (US)
Corresponding author
  • Liu, Peng
  • Yang, Yang
Venue
Science
Published
2023-07-28
Volume
381
Issue
6656
Pages
444-451
ISSN
  • 0036-8075 (ISSN-L)
  • 1095-9203
OpenAlex
W4385298585
Cited by
253
References
123
Citations by year
2026: 80 · 2025: 105 · 2024: 57 · 2023: 11
FWCI
22.35
Type
journal article
Language
en
Open access
Locations
  • Science (publishedVersion)
  • PubMed (publishedVersion)
  • PubMed Central (acceptedVersion)
Funders
  • National Science Foundation (1933487)
  • University of Pittsburgh
  • Herman Frasch Foundation for Chemical Research (947-HF22)
  • Xiamen University
  • National Institutes of Health
  • University of California, Santa Barbara
  • National Institute of General Medical Sciences (R35GM147387, R35GM128779)
  • Division of Materials Research (. DMR-1933487, 1933487)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Enzyme Catalysis and Immobilization
  • Physical Sciences › Chemistry › Organic Chemistry › Radical Photochemical Reactions
  • Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
Keywords
unnatural amino acids, photoredox catalysis, asymmetric catalysis, radical intermediates, engineered enzymes
MeSH terms
Amino Acids, Pyridoxal Phosphate, Stereoisomerism, Biocatalysis

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