Inverted Binding of Non-natural Substrates in Strictosidine Synthase Leads to a Switch of Stereochemical Outcome in Enzyme-Catalyzed Pictet–Spengler Reactions
Elisabeth Eger, Adam Simon, Mahima Sharma, Song Yang, Willem B. Breukelaar, Gideon Grogan, K. N. Houk, Wolfgang Kroutil
Abstract
)-product in those cases. The study demonstrates that the same catalyst can have two different productive binding modes for one substrate but give different absolute configuration of the products by binding the aldehyde substrate differently. These results will guide future engineering of STRs and related enzymes for biocatalytic applications.
Topics & Concepts
TryptamineChemistryPictet–Spengler reactionAldehydeIsoquinolineSubstrate (aquarium)EnzymeTryptaminesCatalysisStereochemistryIndole testBiosynthesisOrganic chemistryBiochemistryOceanographyGeologyMicrobial Natural Products and BiosynthesisAlkaloids: synthesis and pharmacologyBerberine and alkaloids research