4-(benzyloxycarbonylamino)-N-{tris[13-(β-D-galactopyranosyloxy)-2,6,10-trioxatridecyl]methyl}butyramide | 1038802-15-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(benzyloxycarbonylamino)-N-{tris[13-(β-D-galactopyranosyloxy)-2,6,10-trioxatridecyl]methyl}butyramide
• CAS: 1038802-15-1
• 化学式: C₆₁H₁₀₈N₂O₃₀
• 分子量: 1349.52
• InChiKey: HMRZEEXKRIQWIA-VCQKQNJNSA-N

反应信息

• 作为反应物：
  描述：

  4-(benzyloxycarbonylamino)-N-{tris[13-(β-D-galactopyranosyloxy)-2,6,10-trioxatridecyl]methyl}butyramide 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以87%的产率得到4-amino-N-{tris[13-(β-D-galactopyranosyloxy)-2,6,10-trioxatridecyl]methyl}butyramide
  参考文献：
  名称：

  Trivalent, Gal/GalNAc-containing ligands designed for the asialoglycoprotein receptor

  摘要：

  A series of novel, fluorescent ligands designed to bind with high affinity and specificity to the asialoglycoprotein receptor (ASGP-R) has been synthesized and tested on human liver cells. The compounds bear three non-reducing, beta-linked Gal or GalNAc moieties linked to flexible spacers for an optimal spatial interaction with the binding site of the ASGP-R. The final constructs were selectively endocytosed by HepG2 cells derived from parenchymal liver cells-the major human liver cell type-in a process that was visualized with the aid of fluorescence microscopy. Furthermore, the internalization was analyzed with flow cytometry, which showed the process to be receptor-mediated and selective. The compounds described in this work could serve as valuable tools for studying hepatic endocytosis, and are suited as carriers for site-specific drug delivery to the liver. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.017
• 作为产物：
  描述：

  N-{tris[13-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyloxy)-2,6,10-trioxatridecyl]methyl}-4-(benzyloxycarbonylamino)butyramide 在 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 4.0h， 以94%的产率得到4-(benzyloxycarbonylamino)-N-{tris[13-(β-D-galactopyranosyloxy)-2,6,10-trioxatridecyl]methyl}butyramide
  参考文献：
  名称：

  Trivalent, Gal/GalNAc-containing ligands designed for the asialoglycoprotein receptor

  摘要：

  A series of novel, fluorescent ligands designed to bind with high affinity and specificity to the asialoglycoprotein receptor (ASGP-R) has been synthesized and tested on human liver cells. The compounds bear three non-reducing, beta-linked Gal or GalNAc moieties linked to flexible spacers for an optimal spatial interaction with the binding site of the ASGP-R. The final constructs were selectively endocytosed by HepG2 cells derived from parenchymal liver cells-the major human liver cell type-in a process that was visualized with the aid of fluorescence microscopy. Furthermore, the internalization was analyzed with flow cytometry, which showed the process to be receptor-mediated and selective. The compounds described in this work could serve as valuable tools for studying hepatic endocytosis, and are suited as carriers for site-specific drug delivery to the liver. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.017