α-Man-(1->3)-β-Glcp-(1->4)-GlcpNAc | 1065008-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-Man-(1->3)-β-Glcp-(1->4)-GlcpNAc
• 英文别名: (2R,3S,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[[(3aR,5R,6S,7R,7aR)-7-hydroxy-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-6-yl]oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1065008-98-1
• 化学式: C₂₀H₃₃NO₁₅
• 分子量: 527.48
• InChiKey: YQSFETVFAHFCJU-GUNYDSGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  250
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  α-Man-(1->3)-β-Glcp-(1->4)-GlcpNAc 、 Nα-(benzyloxycarbonyl)-Nγ-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine O-methyl ester 在 endohexosaminidase M 作用下， 反应 3.0h， 以88%的产率得到N4-[α-D-mannopyranosyl-(1->3)-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl]-N2-(benzyloxycarbonyl)-L-asparagine methyl ester
  参考文献：
  名称：

  内己糖胺酶催化的恶唑啉供体糖基化：催化效率和可逆性的微调。

  摘要：

  合成了一系列完整的恶唑啉二糖、三糖、四糖和六糖，对应于 N-连接糖蛋白高甘露糖聚糖的核心部分，以及相应的含有中心葡萄糖单元的寡糖，并作为糖基供体进行了测试。由内己糖胺酶 M (Endo M)、A (Endo A) 和 H (Endo H) 催化的 GlcNAcAsn 糖基氨基酸的糖基化。虽然 Endo H 没有催化任何糖基化反应，但 Endo M 和 Endo A 都有效地催化了糖基化，这些糖基化不仅限于包含 Manbeta(1-->4)GlcNAc 链接的供体。精确的结构活性关系和时间进程研究揭示了与所用酶和精确恶唑啉结构相关的合成过程效率的微调。Endo M 和 Endo A 均可实现有效的不可逆糖基化，进一步证明使用结构修饰的恶唑啉供体作为过渡态模拟物以促进酶催化合成，同时防止产物水解；在这些情况下，酶表现出“糖基连接酶”活性。

  DOI：

  10.1002/chem.200800365

文献信息

• Endo-β-N-acetylglucosaminidase-catalyzed polymerization of β-Glcp-(1→4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation
  作者：Hirofumi Ochiai、Wei Huang、Lai-Xi Wang

  DOI：10.1016/j.carres.2009.01.016

  日期：2009.3

  An alternative synthesis of beta-Glcp-(1 -> 4)-GlcpNAc oxazoline is described, and its enzymatic reaction with the endo-beta-N-acetylglucosaminidase from Arthrobacter protophormiae (Endo-A) was re-investigated. Under normal transglycosylation conditions with a catalytic amount of enzyme, Enclo-A showed only marginal activity for transglycosylation with the disaccharide oxazoline, consistent with our previous observations. However, when used in a relatively large quantity, Endo-A could promote the transglycosylation of the disaccharide oxazoline to a GlcpNAc-Asn acceptor. In addition to the initial transglycosylation product, a series of large oligosaccharides were also formed due to the tandem transglycosylation to the terminal glucose residues in the intermediate products. In the absence of an external acceptor, Enclo-A could polymerize the disaccharide oxazoline to form oligo- and polysaccharides having the -4-beta-(Glcp-(1 -> 4)-beta-GlcpNAc)-1-repeating units. This is the first example of an endo-beta-N-acetylglucosaminidase-promoted polymerization of activated oligosaccharide substrates. This enzymatic polymerization may find useful applications for the synthesis of novel artificial polysaccharides. (C) 2009 Elsevier Ltd. All rights reserved.