Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Regular issue | Vol 27, No. 3, 1988, pp.613-620
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4409
Alkaloid Production in Catharanthus roseus (L.) G. Don Cell Cultures. XIV. The Role of Unstable Dihydropyridinium Intermediates in the Biosynthesis of Bisindole Alkaloids

James Peter Kutney,* Camille Andre Boulet, Lewis Siu Leung Choi, Wlodzimierz Gustowski, Michael McHugh, Jun Nakano, Tamotsu Nikaido, Hiroki Tsukamoto, Gary Maxwell Hewitt, and Roger Suen

*Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, B.C., V6T 1Z1, Canada

Abstract

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.