Mahboobi, Siavosh and Dove, Stefan and Bednarski, P. J. and Kuhr, S. and Burgemeister, Thomas and Schollmeyer, D. (1997) X-Ray Crystal Structure of Woodinine and Conformational Analysis by Means of Semiempirical and 1H-NMR Methods. Journal of Natural Products-Copublished with the Am. Soc. of Pharmacognosy 60 (6), pp. 587-591.
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The mol. structure of (-)-woodinine (I), a carboline-based alkaloid with antibacterial and antimycobacterial activities, was investigated by X-ray crystallog., NMR, and semiempirical quantum chem. methods. The X-ray crystal structure of I showed the indole ring in the expected planar conformation, the pyrrolidine ring in an envelope conformation, and a weak intramol. hydrogen bond between the pyrrolidine nitrogen and the proton of the indole nitrogen. NMR expts. indicated that this hydrogen bond is not present in soln. and that further differences exist between the crystal and the soln. structures of I. By semiempirical quantum chem. methods, different local energy min. conformations of I, resulting from inversions within the piperidine moiety and from rotation of the pyrrolidine ring, were calcd. The totality of all NOE signals can only be explained to originate from a population of some of these conformers, and addnl. from different envelope and twisted conformations of the pyrrolidine ring.
|Institutions:|| Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer) |
Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry I (Prof. Elz)
|Subjects:||500 Science > 570 Life sciences|
500 Science > 540 Chemistry & allied sciences
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Owner:||Prof. Dr. Stefan Dove|
|Deposited On:||20 Jan 2009 16:48|
|Last Modified:||05 Aug 2009 13:50|