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Stereoselective amino acid synthesis by synergistic photoredox-pyridoxal radical biocatalysis
Open accessAbstract
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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Metadata
- 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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