methyl O-(2,3,4-tri-O-acetyl-6-O-tetrahydropyranyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside | 152698-49-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3,4-tri-O-acetyl-6-O-tetrahydropyranyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-6-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(oxan-2-yloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 152698-49-2
• 化学式: C₃₀H₄₅NO₁₇
• 分子量: 691.684
• InChiKey: KWJGKQGTMJGRQK-REJJZZOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  48.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  215.98
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3,4-tri-O-acetyl-6-O-tetrahydropyranyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以86%的产率得到methyl O-(6-O-tetrahydropyranyl-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Characterization of inhibitory activities and binding mode of synthetic 6′-modified methyl N-acetyl-β-lactosaminide toward rat liver CMP-d-Neu5Ac: d-galactoside-(2 → 6)-α-d-sialyltransferase

  摘要：

  6'-Deoxy (12), 6'-thio (13), and 6'-O-tetrahydropyranosyl (14) analogues of methyl N-acetyl-beta-lactosaminide (3), were synthesized from lactose. NOE experiments proved that they adopt the same conformation as that of 3. Inhibition studies using these synthetic analogues, including the disulfide dimer 15, toward (2 --> 6)-alpha-sialyltransferase (EC 2.4.99.1) revealed that the 6'-deoxy analogue 12 had remarkable inhibitory activity as the first acceptor-analogue inhibitor for this enzyme. It is noteworthy that the disulfide 15 also behaves as an inhibitor. The results indicated that chemical modification at the 6'-position of 3 did not cause much decrease in the binding affinity to the sialyltransferase. Further, a novel possibility that the acceptor and the acceptor-analogue inhibitor can bind simultaneously to the sialyltransferase was proposed based on the inhibition studies with 12 and CMP.

  DOI：

  10.1016/0008-6215(93)84251-z
• 作为产物：
  描述：

  methyl O-(2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside 在 4-甲基苯磺酸吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 methyl O-(2,3,4-tri-O-acetyl-6-O-tetrahydropyranyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Characterization of inhibitory activities and binding mode of synthetic 6′-modified methyl N-acetyl-β-lactosaminide toward rat liver CMP-d-Neu5Ac: d-galactoside-(2 → 6)-α-d-sialyltransferase

  摘要：

  6'-Deoxy (12), 6'-thio (13), and 6'-O-tetrahydropyranosyl (14) analogues of methyl N-acetyl-beta-lactosaminide (3), were synthesized from lactose. NOE experiments proved that they adopt the same conformation as that of 3. Inhibition studies using these synthetic analogues, including the disulfide dimer 15, toward (2 --> 6)-alpha-sialyltransferase (EC 2.4.99.1) revealed that the 6'-deoxy analogue 12 had remarkable inhibitory activity as the first acceptor-analogue inhibitor for this enzyme. It is noteworthy that the disulfide 15 also behaves as an inhibitor. The results indicated that chemical modification at the 6'-position of 3 did not cause much decrease in the binding affinity to the sialyltransferase. Further, a novel possibility that the acceptor and the acceptor-analogue inhibitor can bind simultaneously to the sialyltransferase was proposed based on the inhibition studies with 12 and CMP.

  DOI：

  10.1016/0008-6215(93)84251-z