methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-L-galactopyranosyl)-β-D-glucopyranoside | 71692-91-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-L-galactopyranosyl)-β-D-glucopyranoside
• CAS: 71692-91-6；118451-90-4；122992-46-5；134296-61-0
• 化学式: C₄₂H₅₀O₁₅
• 分子量: 794.85
• InChiKey: JAWOVLHUOOSOEG-GCPPGDMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  57.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  169.81
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-L-galactopyranosyl)-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-α-D-mannopyranosyl-α-D-mannopyranoside
  参考文献：
  名称：

  Lysosomal-enzyme targeting: the phosphorylation of synthetic d-mannosyl saccharides by UDP-N-acetylglucosamine:lysosomal-enzyme N-acetylglucosaminephosphotransferase from rat-liver microsomes and fibroblasts

  摘要：

  Phosphorylation of the D-mannose residues of lysosomal enzymes is essential for the uptake and intracellular transport of these enzymes to lysosomes. The GlcNAc-P-transferase which is involved in the phosphorylation reaction seems to recognize a signal, probably a protein conformation, common to many lysosomal enzymes. To evaluate the role of the carbohydrate portion of the enzyme in these phosphorylation reactions, the acceptor specificity of GlcNAc-P-transferase from rat-liver microsomes and fibroblasts was examined with the aid of synthetic D-mannosyl disaccharides and derivatives that are closely related to the high-mannose type of oligosaccharides. Four methyl D-mannobiosides were synthesized, and their structures were established by 13C-n.m.r. spectroscopy. Of all the D-mannosyl saccharides tested, alpha-D-Man-(1----2)-alpha-D-Man-(1----OMe) was found to be the best acceptor, thereby suggesting that oligosaccharide structure may also have a role to play in recognition by this enzyme.

  DOI：

  10.1016/s0008-6215(00)90298-2
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 在 3 A molecular sieve 、 4 A molecular sieve 、 氰化汞 、 sodium cyanoborohydride 、 mercury dibromide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.5h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-L-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Lysosomal-enzyme targeting: the phosphorylation of synthetic d-mannosyl saccharides by UDP-N-acetylglucosamine:lysosomal-enzyme N-acetylglucosaminephosphotransferase from rat-liver microsomes and fibroblasts

  摘要：

  Phosphorylation of the D-mannose residues of lysosomal enzymes is essential for the uptake and intracellular transport of these enzymes to lysosomes. The GlcNAc-P-transferase which is involved in the phosphorylation reaction seems to recognize a signal, probably a protein conformation, common to many lysosomal enzymes. To evaluate the role of the carbohydrate portion of the enzyme in these phosphorylation reactions, the acceptor specificity of GlcNAc-P-transferase from rat-liver microsomes and fibroblasts was examined with the aid of synthetic D-mannosyl disaccharides and derivatives that are closely related to the high-mannose type of oligosaccharides. Four methyl D-mannobiosides were synthesized, and their structures were established by 13C-n.m.r. spectroscopy. Of all the D-mannosyl saccharides tested, alpha-D-Man-(1----2)-alpha-D-Man-(1----OMe) was found to be the best acceptor, thereby suggesting that oligosaccharide structure may also have a role to play in recognition by this enzyme.

  DOI：

  10.1016/s0008-6215(00)90298-2