(+)-shikonin N-acetyl β-glucosaminoside | 1360441-15-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-shikonin N-acetyl β-glucosaminoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 1360441-15-1
• 化学式: C₂₄H₂₉NO₁₀
• 分子量: 491.495
• InChiKey: BBYKOTCSDVQQAX-VVGGGAQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 碳酸氢钠 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+)-shikonin N-acetyl β-glucosaminoside
  参考文献：
  名称：

  Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

  摘要：

  The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.143

文献信息

• Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin
  作者：Hao He、Li-Ping Bai、Zhi-Hong Jiang

  DOI：10.1016/j.bmcl.2011.12.143

  日期：2012.2

  The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity. (C) 2012 Elsevier Ltd. All rights reserved.