期刊
ACS CATALYSIS
卷 6, 期 1, 页码 23-30出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b01839
关键词
indole alkaloids; strictosidine synthase; transaminases; biocatalytic cascade; strictosidine derivatives
资金
- European Union [289646]
(S)-Strictosidine represents the first key intermediate in the biosynthesis of several pharmaceutically relevant monoterpenoid indole alkaloids. Optically pure C3-methyl-substituted strictosidine derivatives were prepared by setting up the two stereogenic centers at the beta-carboline core via two enzymatic steps catalyzed by the enzymes transaminase and strictosidine synthase in a one-pot cascade fashion. The two enzymatic steps were performed simultaneously as well as in a stepwise fashion. The amination of the prochiral ketones led to optically pure amines with up to >98% enantiomeric excess. Depending on the enzyme used, the (S)- and (R)- enantiomers were prepared in most cases. Selected amines were then condensed with secologanin in a Pictet-Spengler reaction catalyzed by strictosidine synthase leading to diastereomerically pure products (>98% diastereomeric excess).
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