methyl O-(2,3,4-tri-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside | 152501-22-9

• 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-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 2,3,4-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2-deoxy-2-acetamido-3,6-di-O-acetylmethyl-β-D-glucopyranoside；Gal2Ac3Ac4Ac(b1-4)b-GlcNAc1Me3Ac6Ac；[(2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-6-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 152501-22-9
• 化学式: C₂₅H₃₇NO₁₆
• 分子量: 607.566
• InChiKey: QREVTWFLGPARCN-RVPIHWIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  218
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3,4-tri-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 dithiothreitol 作用下， 以 甲醇 、 氘代氯仿 为溶剂， 反应 26.0h， 生成 methyl O-(6-thio-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：

  在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.8h， 生成 methyl O-(2,3,4-tri-O-acetyl-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

文献信息

• Regioselective Deprotection of Peracetylated Disaccharides at the Primary Position Catalyzed by Immobilized Acetyl Xylan Esterase from Bacillus pumilus
  作者：Teodora Bavaro、Marco Filice、Paolo Bonomi、Qais Abu alassal、Giovanna Speranza、Jose M. Guisan、Marco Terreni

  DOI：10.1002/ejoc.201100944

  日期：2011.11

  In this work peracetylated lactose and related compounds have been tested as advanced intermediate substrates in enzymatic deprotections catalyzed by acetyl xylan esterase (AXE) from Bacillus pumilus. In particular, we present a simple and efficient enzymatic procedure to obtain products bearing only one free primary hydroxy group in the C6′ position of the galactoside moiety of “lacto” carbohydrates

  在这项工作中，全乙酰化乳糖和相关化合物已被测试为高级中间底物，用于由来自短小芽孢杆菌的乙酰木聚糖酯酶 (AXE) 催化的酶促脱保护。特别是，我们提出了一种简单有效的酶促程序，以获得在“乳”碳水化合物的半乳糖苷部分的 C6' 位置仅带有一个游离伯羟基的产物。特别是，在 1-O-甲基乳糖胺和六乙酰乳醛的水解中取得了良好的产率（60-70%）。获得的产品作为用于合成非常重要的生物相关寡糖的高级构建模块引起了极大的兴趣。