2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose | 191532-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose
• CAS: 191532-26-0
• 化学式: C₂₈H₃₉NO₁₈
• 分子量: 677.614
• InChiKey: XKTWMUHXXMTTHP-JCCUTGQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  240.89
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose 在 2,4,6-三甲基吡啶 、 三甲基溴硅烷 、 三氟化硼乙醚 作用下， 以 1,1-二氯乙烷 为溶剂， 以64%的产率得到2-methyl-4,5-dihydro-[4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-di-O-acetyl-1,2-dideoxy-α-D-glucopyranoso][2,1-d]-1,3-oxazole
  参考文献：
  名称：

  Endo-β-N-acetylglucosaminidase-catalyzed polymerization of β-Glcp-(1→4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation

  摘要：

  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.

  DOI：

  10.1016/j.carres.2009.01.016
• 作为产物：
  描述：

  β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-D-glucopyranose 、 乙酸酐 在 吡啶 作用下， 以152 mg的产率得到2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Endo-β-N-acetylglucosaminidase-catalyzed polymerization of β-Glcp-(1→4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation

  摘要：

  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.

  DOI：

  10.1016/j.carres.2009.01.016