Inverted Binding of Non-natural Substrates in Strictosidine Synthase Leads to a Switch of Stereochemical Outcome in Enzyme-Catalyzed Pictet–Spengler Reactions

[Image: see text] The Pictet–Spengler reaction is a valuable route to 1,2,3,4-tetrahydro-β-carboline (THBC) and isoquinoline scaffolds found in many important pharmaceuticals. Strictosidine synthase (STR) catalyzes the Pictet–Spengler condensation of tryptamine and the aldehyde secologanin to give (...

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Bibliographic Details
Published in:J Am Chem Soc
Main Authors: Eger, Elisabeth, Simon, Adam, Sharma, Mahima, Yang, Song, Breukelaar, Willem B., Grogan, Gideon, Houk, K. N., Kroutil, Wolfgang
Format: Artigo
Language:Inglês
Published: American Chemical Society 2020
Online Access:https://ncbi.nlm.nih.gov/pmc/articles/PMC6966912/
https://ncbi.nlm.nih.gov/pubmed/31909617
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1021/jacs.9b08704
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