Stereoselective amino acid synthesis by synergistic photoredox-pyridoxal radical biocatalysis
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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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- 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
- PMC
- PMC10444520
- 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
- green
- www.ncbi.nlm.nih.gov
- 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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