Conformational control in the rebeccamycin class of indolocarbazole glycosides

被引:39
作者
Gilbert, EJ [1 ]
Chisholm, JD [1 ]
Van Vranken, DL [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
D O I
10.1021/jo990296v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:5670 / 5676
页数:7
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