β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-[α-D-neuraminyl-(2->3)]-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-[1-14C]octadecanamido-4-octadecen-1,3-diol | 190901-50-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-[α-D-neuraminyl-(2->3)]-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-[1-14C]octadecanamido-4-octadecen-1,3-diol
• CAS: 190901-50-9
• 化学式: C₇₁H₁₂₉N₃O₃₀
• 分子量: 1506.8
• InChiKey: DUQGUEDHUJDMJK-HGUJOQTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.22
• 重原子数：
  104.0
• 可旋转键数：
  51.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  537.5
• 氢给体数：
  20.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  生物素化-epsilon-氨基己酸-N-羟基丁二酰亚胺活化酯 、 β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-[α-D-neuraminyl-(2->3)]-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-[1-14C]octadecanamido-4-octadecen-1,3-diol 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以21.7%的产率得到β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-[N-D-biotinyl-ε-amidocaproyl-α-D-neuraminyl-(2->3)]-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-[1-14C]octadecanamido-4-octadecen-1,3-diol
  参考文献：
  名称：

  Synthesis and mass spectrometric characterization of digoxigenin and biotin labeled ganglioside GM I and their uptake by and metabolism in cultured cells

  摘要：

  Selective acylation of mono-deacetyl lyso-GM1, i.e. beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-galactopyranosyl-(1 --> 4)-(alpha-D-neuraminyl-(2 --> 3))-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 1)-(2S,3R,4E)-2-amino-4-octadecen-1,3-diol, with N-succinimidyl-[1-C-14]stearate afforded labeled mono-deacetyl GM1, i.e. beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-galactopyranosyl-(1 --> 4)-(alpha-D-neuraminyl-(2 --> 3))-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 1)-(2S,3R,4E)-2-[1-C-14]octadecanamido-4-octadecen-1,3-diol, in good yield. Its condensation with either N-succinimidyl-digoxigenyl-3-O-methyl carbonyl-epsilon-amino caproate or N-succinimidyl-D-biotinyl-epsilon-aminocaproate led to radioactive GM1 derivatives carrying a tag for immune-electron microscopy at the sialic acid residue. These GM1 derivatives could be hydrolyzed to the corresponding GM3 derivatives by treatment with GM1-beta-galactosidase and beta-hexosaminidases. There was no further degradation by sialidases due to the bulky tag in the sialic acid residue. The uptake of biotin labeled GM1 by human skin fibroblasts, rat neuroblastoma cells B104 and human neuroblastoma cells SHSY5Y was 0.85, 0.58 and 1.62 nmol lipid/mg cellular protein, respectively, after an incubation for 66 h at 37 degrees C and was similar to that of untagged GM1. The uptake of digoxigenin labeled GM1 by these cell types was, however, significantly higher (3.1, 6.8, and 20.0 nmol lipid/mg cellular protein, respectively). Both the biotin and digoxigenin labeled GM1 analogs were catabolized to the corresponding GM2 and GM3 derivatives in lysosomes of cultured cells. This demonstrates that these synthetic analogues are suitable for studying, by immune-electron microscopy, their endocytosis and distribution in intralysosomal membranes. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)02658-3
• 作为产物：
  描述：

  N-succinimidyl-[1-14C]stearate 、 β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-[α-D-neuraminyl-(2->3)]-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-amino-4-octadecen-1,3-diol 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-[α-D-neuraminyl-(2->3)]-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-[1-14C]octadecanamido-4-octadecen-1,3-diol
  参考文献：
  名称：

  Synthesis and mass spectrometric characterization of digoxigenin and biotin labeled ganglioside GM I and their uptake by and metabolism in cultured cells

  摘要：

  Selective acylation of mono-deacetyl lyso-GM1, i.e. beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-galactopyranosyl-(1 --> 4)-(alpha-D-neuraminyl-(2 --> 3))-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 1)-(2S,3R,4E)-2-amino-4-octadecen-1,3-diol, with N-succinimidyl-[1-C-14]stearate afforded labeled mono-deacetyl GM1, i.e. beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-galactopyranosyl-(1 --> 4)-(alpha-D-neuraminyl-(2 --> 3))-beta-D-galactopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 1)-(2S,3R,4E)-2-[1-C-14]octadecanamido-4-octadecen-1,3-diol, in good yield. Its condensation with either N-succinimidyl-digoxigenyl-3-O-methyl carbonyl-epsilon-amino caproate or N-succinimidyl-D-biotinyl-epsilon-aminocaproate led to radioactive GM1 derivatives carrying a tag for immune-electron microscopy at the sialic acid residue. These GM1 derivatives could be hydrolyzed to the corresponding GM3 derivatives by treatment with GM1-beta-galactosidase and beta-hexosaminidases. There was no further degradation by sialidases due to the bulky tag in the sialic acid residue. The uptake of biotin labeled GM1 by human skin fibroblasts, rat neuroblastoma cells B104 and human neuroblastoma cells SHSY5Y was 0.85, 0.58 and 1.62 nmol lipid/mg cellular protein, respectively, after an incubation for 66 h at 37 degrees C and was similar to that of untagged GM1. The uptake of digoxigenin labeled GM1 by these cell types was, however, significantly higher (3.1, 6.8, and 20.0 nmol lipid/mg cellular protein, respectively). Both the biotin and digoxigenin labeled GM1 analogs were catabolized to the corresponding GM2 and GM3 derivatives in lysosomes of cultured cells. This demonstrates that these synthetic analogues are suitable for studying, by immune-electron microscopy, their endocytosis and distribution in intralysosomal membranes. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)02658-3