Conformational Control in the Rebeccamycin Class of Indolocarbazole Glycosides.
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.
Gilbert
Eric J.
EJ
Department of Chemistry, The University of California, Irvine, California 92697-2025.
Chisholm
John D.
JD
Van Vranken
David L.
DL