11-D-biotinamide-N-[3,6,9-trioxaundecane]-1-amino-1-deoxycellitol | 418759-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 11-D-biotinamide-N-[3,6,9-trioxaundecane]-1-amino-1-deoxycellitol
• CAS: 418759-46-3
• 化学式: C₃₀H₅₆N₄O₁₅S
• 分子量: 744.858
• InChiKey: NOBIJAIAJNPLPB-BGMLZUIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.27
• 重原子数：
  50.0
• 可旋转键数：
  26.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  290.25
• 氢给体数：
  12.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  perfluorophenyl palmitate 、 11-D-biotinamide-N-[3,6,9-trioxaundecane]-1-amino-1-deoxycellitol 在 TEA 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以2.6 mg的产率得到11-D-biotinamide-N-[3,6,9-trioxaundecane]-N-palmitoyl-1-amino-1-deoxycellitol
  参考文献：
  名称：

  Non-Natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant Gp120

  摘要：

  Interactions of recombinant gp120 (rgp120) with non-natural glycosphingolipids (GSLs) and structurally simpler analogues have been studied using a competitive adhesion assay. Conjugates of cellobiosyl ceramide and melibiosyl ceramide were synthetically prepared as water-soluble GSL analogues. These ligands were screened against a panel of biologically relevant analogues, and the results show that their interactions with rgp120 are comparable to natural cellular receptors. Glycolipid interactions with rgp120 were probed further by the synthesis and testing of structurally simpler analogues that were obtained by reductive amination of lactose, cellobiose, and melibiose with a biotinylated amino ethylene glycol moiety. RGp120 did not recognize conjugates lacking a lipid component. However. palmitoylation of the secondary amino alditols yielded compounds with comparable rgp120 affinity to the natural cellular receptor. galactosyl ceramide (GalCer). Taken together, the SAR showed that both a hydrophobic and it hydrophilic component are required for rgp120 recognition. Moreover. structural variability in the carbohydrate headgroup did not significantly alter rgp120 recognition indicating that this interaction is not highly specific. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00325-x
• 作为产物：
  描述：

  N-Boc-N'-biotinyl-3,6,9-trioxaundecane-1,11-diamine 在 reaget K²⁵ 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 生成 11-D-biotinamide-N-[3,6,9-trioxaundecane]-1-amino-1-deoxycellitol
  参考文献：
  名称：

  Non-Natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant Gp120

  摘要：

  Interactions of recombinant gp120 (rgp120) with non-natural glycosphingolipids (GSLs) and structurally simpler analogues have been studied using a competitive adhesion assay. Conjugates of cellobiosyl ceramide and melibiosyl ceramide were synthetically prepared as water-soluble GSL analogues. These ligands were screened against a panel of biologically relevant analogues, and the results show that their interactions with rgp120 are comparable to natural cellular receptors. Glycolipid interactions with rgp120 were probed further by the synthesis and testing of structurally simpler analogues that were obtained by reductive amination of lactose, cellobiose, and melibiose with a biotinylated amino ethylene glycol moiety. RGp120 did not recognize conjugates lacking a lipid component. However. palmitoylation of the secondary amino alditols yielded compounds with comparable rgp120 affinity to the natural cellular receptor. galactosyl ceramide (GalCer). Taken together, the SAR showed that both a hydrophobic and it hydrophilic component are required for rgp120 recognition. Moreover. structural variability in the carbohydrate headgroup did not significantly alter rgp120 recognition indicating that this interaction is not highly specific. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00325-x