octyl 2,3,4-tri-O-methyl-β-D-glucopyranoside | 151902-32-8

• 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: octyl 2,3,4-tri-O-methyl-β-D-glucopyranoside
• CAS: 151902-32-8
• 化学式: C₁₇H₃₄O₆
• 分子量: 334.453
• InChiKey: DTMUOBVQAOWJFU-NQNKBUKLSA-N

物化性质

• 沸点：
  418.8±45.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  23.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  octyl 2,3,4-tri-O-methyl-β-D-glucopyranoside 在 甲醇 、 4 A molecular sieve 、 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 硝基甲烷 、 苯 为溶剂， 反应 32.0h， 生成 octyl 6-O-<2-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranosyl>-2,3,4-tri-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Recognition of the acceptor β-d-Glc pNAc-(1 → 2)-α-d-Manp(1 → 6)-β-d-Glc p-OR by N-acetylglucosaminyltransferase-V: None of the hydroxyl groups on the Glc-residue are important

  摘要：

  The enzyme, N-acetylglucosaminyltransferase-V (GlcNAcT-V, E.C 2.4.1.155), transters a beta-D-GlcpNAc residue, from UDP-GlcNAc, to the OH-6 group of the Man residue in the synthetic acceptor beta-D-GlcpNAc-(1 --> 2)-alpha-D-Manp-(l --> 6)-beta-D-Glcp-O(CH2)7CH3 (3). Trisaccharide 3 is an excellent substrate for the enzyme from hamster kidney with a K(m) value of 26 muM. In this paper we examine the contribution of the Glc residue in 3 to acceptor recognition by this enzyme. Beta-D-GlcpNAc-(1 --> 2)-alpha-D-Manp-O(CH2)7CH3 (5), where the Glc residue in 3 has been deleted, was synthesized and found to be a very poor substrate with a K(m) value elevated to almost 2 mM. Two other analogues of 3, where the Glc residue was 0-trimethylated (6) or 0-tribenzylated (7), respectively, possessed K(m) values very near to those of 3. The Glc residue in 3 is thereby shown to present an important recognition element for GlcNAcT-V, but none of the free hydroxyl groups are required. This observation should facilitate the design of more hydrophobic and membrane-permeable analogues of 3 that are expected to function as specific glycosylation inhibitors.

  DOI：

  10.1016/0008-6215(93)80081-o
• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-3,4,5-Trimethoxy-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-6-octyloxy-tetrahydro-pyran 在 溶剂黄146 作用下， 反应 20.0h， 生成 octyl 2,3,4-tri-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Recognition of the acceptor β-d-Glc pNAc-(1 → 2)-α-d-Manp(1 → 6)-β-d-Glc p-OR by N-acetylglucosaminyltransferase-V: None of the hydroxyl groups on the Glc-residue are important

  摘要：

  The enzyme, N-acetylglucosaminyltransferase-V (GlcNAcT-V, E.C 2.4.1.155), transters a beta-D-GlcpNAc residue, from UDP-GlcNAc, to the OH-6 group of the Man residue in the synthetic acceptor beta-D-GlcpNAc-(1 --> 2)-alpha-D-Manp-(l --> 6)-beta-D-Glcp-O(CH2)7CH3 (3). Trisaccharide 3 is an excellent substrate for the enzyme from hamster kidney with a K(m) value of 26 muM. In this paper we examine the contribution of the Glc residue in 3 to acceptor recognition by this enzyme. Beta-D-GlcpNAc-(1 --> 2)-alpha-D-Manp-O(CH2)7CH3 (5), where the Glc residue in 3 has been deleted, was synthesized and found to be a very poor substrate with a K(m) value elevated to almost 2 mM. Two other analogues of 3, where the Glc residue was 0-trimethylated (6) or 0-tribenzylated (7), respectively, possessed K(m) values very near to those of 3. The Glc residue in 3 is thereby shown to present an important recognition element for GlcNAcT-V, but none of the free hydroxyl groups are required. This observation should facilitate the design of more hydrophobic and membrane-permeable analogues of 3 that are expected to function as specific glycosylation inhibitors.

  DOI：

  10.1016/0008-6215(93)80081-o