Crystal Structure of (−)-Corycavinium (+)-10-Camphorsulfonate, a biosynthetic intermediate to hexahydrobenzo[c]phenanthridine alkaloids
✍ Scribed by Miyoko Kamigauchi; Yuko Noda; Kinuko Iwasa; Zjujiro Nishijo; Toshimasa Ishida; Yasuko In; Wolfgang Wiegrebe
- Book ID
- 102857349
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- German
- Weight
- 532 KB
- Volume
- 77
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
The crystal structure of (−)‐corycavinium (+)‐10‐camphorsulfonate has been investigated by X‐ray analysis. The structure of (−)‐corycavinium ion ( (−)‐(7__S__,13__S__,14__R__)‐5,6,13,13a‐tetrahydro‐13a‐hydroxy‐7‐methyl‐2,3;9,10‐bis(methylenedioxy)‐8__H__‐dibenzo[a,g]quinolizinium), has been determined. The conformation with B/C‐cis‐conjunction, a twisted half‐chair of ring B, and a half‐chair of ring C, as well as α‐oriented substituted groups N…Me, C…Me, and C…OH is revealed. Feeding experiments with cell suspension cultures of Corydalis incisa (Papaveraceae) defined the intermediacy of (−)‐corycavinium in the route from protoberberine‐type to hexahydrobenzo[c]phenanthridine‐type of alkaloids. On the basis of the present crystal conformation, the stereospecificity of the relating enzyme is biogenetically considered.