Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent "ene"-Reductases

Xin Gao, Joshua R. Turek-Herman, Young Joo Choi, Ryan D. Cohen, Todd K. Hyster

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

α-Tertiary amines are a common motif in pharmaceutically important molecules but are challenging to prepare using asymmetric catalysis. Here, we demonstrate engineered flavin-dependent ‘ene'-reductases (EREDs) can catalyze radical additions into oximes to prepare this motif. Two different EREDs were evolved into competent catalysts for this transformation with high levels of stereoselectivity. Mechanistic studies indicate that the oxime contributes to the enzyme templated charge-transfer complex formed between the substrate and cofactor. These products can be further derivatized to prepare a variety of motifs, highlighting the versatility of ERED photoenzymatic catalysis for organic synthesis.

Original languageEnglish (US)
Pages (from-to)19643-19647
Number of pages5
JournalJournal of the American Chemical Society
Volume143
Issue number47
DOIs
StatePublished - Dec 1 2021

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry

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