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A Facile Chemoenzymatic Approach: One‐Step Syntheses of Monoterpenoid Indole Alkaloids
Author(s) -
Zou HongBin,
Zhu HuaJian,
Zhang Liang,
Yang LiuQing,
Yu YongPing,
Stöckigt Joachim
Publication year - 2010
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000520
Subject(s) - tryptamine , indole test , chemistry , stereochemistry , biomimetic synthesis , organic chemistry , combinatorial chemistry , biochemistry
Facile chemoenzymatic syntheses of cytotoxic monoterpenoid indole alkaloids with novel skeletons and multiple chiral centers are described. Synthesis of these alkaloids was achieved by a simple one‐step reaction using strictosidine and 12‐aza‐strictosidine as the key intermediates. Strictosidines were prepared by coupling of secologanin with tryptamine and 7‐aza‐tryptamine, respectively, using the immobilized recombinant Rauvolfia strictosidine synthase. A detailed stereochemical analysis is presented herein. The results provide an opportunity for a chemoenzymatic approach that leads to an increased diversification of complex alkaloids with improved structures and activities.