1355-31-3Relevant articles and documents
ALKALOID PRODUCTION IN CATHARANTHUS ROSEUS (L.) G. DON CELL CULTURES. XIV. THE ROLE OF UNSTABLE DIHYDROPYRIDINIUM INTERMEDIATES IN THE BIOSYNTHESIS OF BISINDOLE ALKALOIDS
Kutney, James Peter,Boulet, Camille Andre,Choi, Lewis Siu Leung,Gustowski, Wlodzimierz,McHugh, Michael,et al.
, p. 613 - 620 (2007/10/02)
Employing enzyme systems obtained from Catharanthus roseus cell cultures, experiments relating to the biosynthesis of various bisindole alkaloids are described.Specifically, the enzyme-catalyzed coupling of catharanthine (1) and vindoline (2) to a highly unstable dihydropyridinium intermediate (9), important in the biosynthesis of 3',4'-anhydrovinblastine (3), leurosine (4), catharine (6), vinamidine (7) and hydroxyvinamidine (8) is presented.Conversions of 9 to these alkaloids and its role in the biosynthesis is discussed.Although catharanthine is well utilized by the enzyme system, catharanthine N-oxide (10), an important intermediate in the chemical coupling of 1 and 2 to afford 9, is not utilized.