Conformational control in the rebeccamycin class of indolocarbazole glycosides

Eric J. Gilbert, John D. Chisholm, David L. Van Vranken

Research output: Contribution to journalArticlepeer-review

42 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)5670-5676
Number of pages7
JournalJournal of Organic Chemistry
Issue number15
StatePublished - Jul 23 1999
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


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