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Conformational Control in the Rebeccamycin Class of Indolocarbazole Glycosides
Eric J. Gilbert1, John D. Chisholm, David L. Van Vranken
1Department of Chemistry, The University of California, Irvine, California 92697-2025.
The Journal of Organic Chemistry
|October 25, 2001
Abstract:
Indolocarbazole glycosides are balanced between two conformations: a "closed" conformation containing a cyclic hydrogen bond between the indolocarbazole NH and the pyranose oxygen and an "open" conformation in which the indolocarbazole NH is hydrogen bonded to solvent. The open conformation never has a commanding advantage, even in DMSO, but in nonpolar environments the cyclic conformation predominates.