Kamigauchi, M. and Noda, Y. and Iwasa, K. and Nishijo, Z. and Ishida, T. and In, Y. and Wiegrebe, Wolfgang (1994) Crystal Structure of (-)-Corycavinium(+)-10-Camphorsulfonate, a Biosynthetic Intermediate to Hexahydrobenzo[c]phenanthridine Alkaloids. Helvetica Chimica Acta 77, pp. 243-251.
The crystal structure of (—)-corycavinium (+)-10-camphorsulfonate has been investigated by X-ray analysis.
The structure of (-)-corycavinium ion ( = (-)-(7S,13S,14R)-5,6,13,13a-tetrahydro-l3a-hydroxy-7-methyl-
2,3;9,10-bis(methylenedioxy)-8H-dibenzo[a,g]quinolizinium), has been determined. The conformation with B/Ccis
-conjunction, a twisted half-chair of ring B, and a half-chair of ring C, as well as a -oriented substituted groups
N - M e , C - Me, and C - O H 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.
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Wiegrebe|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||12 Jul 2010 09:41|
|Last Modified:||20 Jul 2011 22:32|