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- W3091592280 abstract "Abstract Stereoselective catalysts for the Pictet–Spengler reaction of tryptamines and aldehydes may allow a simple and fast approach to chiral 1‐substituted tetrahydro‐β‐carbolines. Although biocatalysts have previously been employed for the Pictet–Spengler reaction, not a single one accepts benzaldehyde and its substituted derivatives. To address this challenge, a combination of substrate walking and transfer of beneficial mutations between different wild‐type backbones was used to develop a strictosidine synthase from Rauvolfia serpentina ( Rs STR) into a suitable enzyme for the asymmetric Pictet–Spengler condensation of tryptamine and benzaldehyde derivatives. The double variant Rs STR V176L/V208A accepted various ortho ‐, meta ‐ and para ‐substituted benzaldehydes and produced the corresponding chiral 1‐aryl‐tetrahydro‐β‐carbolines with up to 99 % enantiomeric excess." @default.
- W3091592280 created "2020-10-08" @default.
- W3091592280 creator A5009412615 @default.
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- W3091592280 creator A5084821187 @default.
- W3091592280 creator A5091400511 @default.
- W3091592280 date "2020-11-03" @default.
- W3091592280 modified "2023-10-09" @default.
- W3091592280 title "Asymmetric Biocatalytic Synthesis of 1‐Aryltetrahydro‐β‐carbolines Enabled by “Substrate Walking”" @default.
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- W3091592280 doi "https://doi.org/10.1002/chem.202004449" @default.
- W3091592280 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/7756766" @default.
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- W3091592280 hasPublicationYear "2020" @default.
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