A facile chemoenzymatic approach: one-step syntheses of monoterpenoid indole alkaloids.
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.
Zou
Hong-Bin
HB
College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
Zhu
Hua-Jian
HJ
Zhang
Liang
L
Yang
Liu-Qing
LQ
Yu
Yong-Ping
YP
Stöckigt
Joachim
J
D001372:Aza Compounds / Q000737:chemistry; D055162:Biocatalysis; D019759:Carbon-Nitrogen Lyases / Q000737:chemistry*; D004800:Enzymes, Immobilized / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011926:Rauwolfia / Q000201:enzymology; D011994:Recombinant Proteins / Q000737:chemistry; D046948:Secologanin Tryptamine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D014748:Vinca Alkaloids / Q000737:chemistry
D001372:Aza Compounds; D004800:Enzymes, Immobilized; D011994:Recombinant Proteins; D046948:Secologanin Tryptamine Alkaloids; D014748:Vinca Alkaloids; C021093:strictosidine; D019759:Carbon-Nitrogen Lyases; C022684:strictosidine synthetase