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Enzymatic Kinetic Resolution by Addition of Oxygen

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 9, Pages 4434-4447

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202011468

Keywords

biocatalysis; kinetic resolution; oxidative enzymes; total synthesis

Funding

  1. EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine [EP/L015838/1]
  2. AstraZeneca
  3. Diamond Light Source
  4. Defence Science and Technology Laboratory
  5. Evotec
  6. GlaxoSmithKline
  7. Janssen
  8. Novartis
  9. Pfizer
  10. Syngenta
  11. Takeda
  12. UCB
  13. Vertex

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Kinetic resolution using biocatalysis is an excellent complementary technique to traditional asymmetric catalysis, producing valuable oxygenated structures for synthetic route development. Enzymes catalyzing the insertion of an oxygen atom into the substrate, such as the Baeyer-Villiger rearrangement, epoxidation, and hydroxylation, play a key role in oxidative kinetic resolution. These key enantiomer-enriched intermediates have important applications in natural product synthesis.
Kinetic resolution using biocatalysis has proven to be an excellent complementary technique to traditional asymmetric catalysis for the production of enantioenriched compounds. Resolution using oxidative enzymes produces valuable oxygenated structures for use in synthetic route development. This Minireview focuses on enzymes which catalyse the insertion of an oxygen atom into the substrate and, in so doing, can achieve oxidative kinetic resolution. The Baeyer-Villiger rearrangement, epoxidation, and hydroxylation are included, and biological advancements in enzyme development, and applications of these key enantioenriched intermediates in natural product synthesis are discussed.

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