methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-O-<(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-6)>-O-β-D-galactopyranosyl-(1-4)-β-D-glucopyranoside | 93515-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-O-<(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-6)>-O-β-D-galactopyranosyl-(1-4)-β-D-glucopyranoside
• 英文别名: β-D-GlcpNAc-(1-3)-<β-D-GlcpNAc-(1-6)>-β-D-Galp-(1-4)-β-D-GlcOMe；methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-O-[(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-6)]-O-β-D-galactopyranosyl-(1-4)-β-D-glucopyranoside
• CAS: 93515-07-2
• 化学式: C₂₉H₅₀N₂O₂₁
• 分子量: 762.717
• InChiKey: XEXYXGOVQFNGDU-XFGWDAGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.81
• 重原子数：
  52.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  354.57
• 氢给体数：
  13.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-O-<(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-6)>-O-β-D-galactopyranosyl-(1-4)-β-D-glucopyranoside 、 对氟苯甲醇 在 尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 磷烯醇丙酮酸 、 EC 2.7.7.9 、 EC 3.6.1.1 、 EC 5.1.3.2 、 five immobilized enzymes: EC 2.4.1.22 、 inorganic salts 、 β-烟酰胺腺嘌呤二核苷酸 、 1,4-二巯基-2,3-丁二醇 作用下， 生成 β-D-GlcpNAc-(1-3)-<β-D-Galp-(1-4)-β-D-GlcpNAc-(1-6)>-β-D-Galp-(1-4)-β-D-GlcOMe 、 methyl O-β-D-galactopyranosyl-(1-4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-O-<(β-D-galactopyranosyl)-(1-4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-6)>-O-β-D-galactopyranosyl-(1-4)-β-D-glucopyranoside
  参考文献：
  名称：

  The use of an immobilised cyclic multi-enzyme system to synthesise branched penta- and hexa-saccharides associated with blood-group I epitopes

  摘要：

  The branched hexasaccharide beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----3)- [beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----6)]-beta-D-Galp-(1----4)-beta -D- GlcOMe (1) was obtained on a 0.1-mmol scale by enzymic bigalactosylation of the tetrasaccharide beta-D-GlcpNAc-(1----3)-[beta-D-GlcpNAc-(1----6)]-beta-D-Galp-(1----4)-b eta- D-GlcOMe by the use of an immobilised multi-enzyme system which regenerated UDP-alpha-D-galactose in situ. The formation of 1 proceeded in two steps. An intermediate compound was identified on the basis of 1H- and 13C-n.m.r. data as the pentasaccharide beta-D-GlcpNAc-(1----3)-[beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----6)]-b eta- D-Galp-(1----4)-beta-D-GlcOMe.

  DOI：

  10.1016/s0008-6215(00)90336-7
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-O-<(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-6)>-O-β-D-galactopyranosyl-(1-4)-β-D-glucopyranoside
  参考文献：
  名称：

  乳糖的糖基化：涉及具有I型血活性的糖脂的生物合成中涉及的分支寡糖的合成

  摘要：

  制备4-O-（2-O-苯甲酰基-4,6-O-亚苄基-β-D-吡喃半乳糖基）-2,3,6-三-O-苯甲酰基-β-D-吡喃葡萄糖苷（2）从甲基β-乳糖苷四个步骤。晶体2是用于合成衍生自乳糖的支链寡糖的便利底物。首先，使用N-邻苯二甲酰氨基糖的三氯乙酰亚胺酸酯在3'-位进行高产率的糖基化，然后在除去亚苄基后在6'-位进行。因此，将3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃葡萄糖基三氯乙酰亚氨酸酯用于两个连续的糖基化反应中，同时用于三醇9的同时分解，从而导致每个序列变为支链四糖β-D-GlcpNAc-（1 ---- 3）-[β-D-GlcpNAc-（1 ---- 6）]-β-D-Galp-（1 ---- 4） -β-D-GlcOMe。用3进行相似的糖基化，

  DOI：

  10.1016/s0008-6215(00)90333-1