11-(β-D-glucopyranosyl)-indolo<2,3-a>carbazole | 236750-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 11-(β-D-glucopyranosyl)-indolo<2,3-a>carbazole
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(11H-indolo[2,3-a]carbazol-12-yl)oxane-3,4,5-triol
• CAS: 236750-71-3
• 化学式: C₂₄H₂₂N₂O₅
• 分子量: 418.449
• InChiKey: KMOSOOJLIAWWAV-REXJZNOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  111
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 11-(β-D-glucopyranosyl)-indolo<2,3-a>carbazole 以 吡啶 为溶剂， 反应 24.0h， 以98%的产率得到11-(β-D-tetra-O-acetylglucopyranosyl)-indolo<2,3-a>carbazole
  参考文献：
  名称：

  Conformational Control in the Rebeccamycin Class of Indolocarbazole Glycosides

  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.

  DOI：

  10.1021/jo990296v
• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以73%的产率得到11-(β-D-glucopyranosyl)-indolo<2,3-a>carbazole
  参考文献：
  名称：

  Conformational Control in the Rebeccamycin Class of Indolocarbazole Glycosides

  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.

  DOI：

  10.1021/jo990296v

文献信息

• Natural Product Diversification Using a Non-natural Cofactor Analogue of <i>S</i>-Adenosyl-<scp>l</scp>-methionine
  作者：Changsheng Zhang、Rachel L. Weller、Jon S. Thorson、Scott R. Rajski

  DOI：10.1021/ja056231t

  日期：2006.3.1

  synthetic cofactor bearing a pendant 5'-amino acid N-mustard. Unlike previously studied synthetic cofactors, this material is very efficiently used by the natural product biosynthetic enzyme rebeccamycin methyltransferase (RebM) to generate a number of new rebeccamycin analogues. These data promote the notion that natural product methyltransferases can be used with non-natural cofactors to enhance

  带有 5'-氮丙啶或 5'-N-芥末亲电子试剂的腺苷类似物是甲基转移酶依赖性 DNA 烷化剂。我们在此展示了一种带有悬垂 5'-氨基酸 N-芥末的新型合成辅因子。与先前研究的合成辅因子不同，天然产物生物合成酶瑞贝卡霉素甲基转移酶 (RebM) 非常有效地使用这种材料来生成许多新的瑞贝卡霉素类似物。这些数据促进了天然产物甲基转移酶可与非天然辅因子一起使用以增强天然产物类似物的分子多样性以用于药物发现的概念。据我们所知，这是除 DNA 甲基转移酶之外的第一个生物甲基转移酶的文献，它可以利用这种合成辅因子。
• Conformational Control in the Rebeccamycin Class of Indolocarbazole Glycosides
  作者：Eric J. Gilbert、John D. Chisholm、David L. Van Vranken

  DOI：10.1021/jo990296v

  日期：1999.7.1

  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.