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Why are the terpenoid indole alkaloids of type I homochiral?
Author(s) -
Beke Gyula,
PatthyLukáts Ágnes,
Podányi Benjamin,
Szabó László F.
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.1065
Subject(s) - chemistry , tryptamine , stereoselectivity , stereochemistry , indole test , chirality (physics) , oxindole , indole alkaloid , organic chemistry , catalysis , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
Abstract In the presence of the enzyme strictosidine synthase, the coupling reaction of secologanin and tryptamine is completely stereoselective and affords strictosidine with 3 S configuration, exclusively. The stereoselectivity is transferred and retained in most indole alkaloids of type I in which C‐3 is not involved in subsequent reactions. By using results of model reactions, the stereoselectivity was interpreted by the bulkiness of the enzyme temporarily attached to the N‐4 atom in the formation of the indolenine intermediate. 3 S configuration is kept in the subsequent 1,2‐rearrangement into the β‐carboline structure. In the formation of the oxindole derivatives, the 3 S configuration is preferred, but not necessarily complete. Chirality 13:483–487, 2001. © 2001 Wiley‐Liss, Inc.