D-biotin-12-amido-4,7,10-trioxadodecyl sphingosinamide | 252881-79-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: D-biotin-12-amido-4,7,10-trioxadodecyl sphingosinamide
• CAS: 252881-79-1
• 化学式: C₃₇H₆₈N₄O₈S
• 分子量: 729.035
• InChiKey: ZQUZDRWHBMVTGE-MHZXKFCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  50.0
• 可旋转键数：
  33.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  167.48
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  D-biotin-12-amido-4,7,10-trioxadodecyl sphingosinamide 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 27.0h， 生成 β-D-galactopyranosyl-α-(1-6)-O-(β-D-glucopyranosyl)-(1-1)-(2S,3R,4E)-3-hydroxy-2-N-(12-D-biotinamide-4,7,10-trioxadodecyl)-sphingenine
  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：

  D-鞘氨醇 、 3-[2-(2-{2-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethoxy]-propionic acid 2,3,5,6-tetrafluoro-phenyl ester 在 TEA 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到D-biotin-12-amido-4,7,10-trioxadodecyl sphingosinamide
  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