期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 69, 页码 16281-16285出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202004449
关键词
asymmetric catalysis; biocatalysis; carbolines; enzyme engineering; Pictet– Spengler reaction
资金
- F. Hoffmann-La Roche Funding Source: Medline
Stereoselective catalysts for the Pictet-Spengler reaction of tryptamines and aldehydes may allow a simple and fast approach to chiral 1-substituted tetrahydro-beta-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 (RsSTR) into a suitable enzyme for the asymmetric Pictet-Spengler condensation of tryptamine and benzaldehyde derivatives. The double variant RsSTR V176L/V208A accepted various ortho-, meta- and para-substituted benzaldehydes and produced the corresponding chiral 1-aryl-tetrahydro-beta-carbolines with up to 99 % enantiomeric excess.
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