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Stereodivergent Evolution of Artificial Enzymes for the Michael Reaction.
Journal article

Stereodivergent Evolution of Artificial Enzymes for the Michael Reaction.

  • Garrabou X Laboratory of Organic Chemistry, ETH Zürich, 8093, Zürich, Switzerland.
  • Macdonald DS Laboratory of Organic Chemistry, ETH Zürich, 8093, Zürich, Switzerland.
  • Wicky BIM Laboratory of Organic Chemistry, ETH Zürich, 8093, Zürich, Switzerland.
  • Hilvert D Laboratory of Organic Chemistry, ETH Zürich, 8093, Zürich, Switzerland.
  • 2018-02-16
Published in:
  • Angewandte Chemie (International ed. in English). - 2018
artificial enzymes
asymmetric catalysis
biocatalysis
carboligasse
directed evolution
Biocatalysis
Directed Molecular Evolution
Fructose-Bisphosphate Aldolase
Ketones
Stereoisomerism
English Enzymes are valuable biocatalysts for asymmetric synthesis due to their exacting stereocontrol. Changing the selectivity of an existing catalyst for new applications is, however, challenging. Here we show that, in contrast, the stereoselectivity of an artificial enzyme created by design and directed evolution is readily tunable. We engineered a promiscuous artificial retro-aldolase into four stereocomplementary catalysts for the Michael addition of a tertiary carbanion to an unsaturated ketone. Notably, this selectivity is also preserved with alternative Michael nucleophiles. Complete stereodiversification of other designer enzymes should similarly be possible by extension of these approaches.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/112734
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