2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl chloride | 151902-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl chloride
• CAS: 151902-33-9
• 化学式: C₂₆H₃₆ClNO₁₆
• 分子量: 654.022
• InChiKey: WNLWWVYKWFKLSG-WRATXCPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.58
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  214.59
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl chloride 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-benzyl-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：

  2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,3,4,6-tetra-O-acetyl-α-D-mannopyranose 在 盐酸 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以71%的产率得到2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl chloride
  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