benzyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 1152421-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS: 1152421-42-5
• 化学式: C₆₃H₅₉NO₁₅
• 分子量: 1070.16
• InChiKey: OCZHBZSLRIERTH-BANGSXEGSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.88
• 重原子数：
  79.0
• 可旋转键数：
  22.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  189.68
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  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：

  benzyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 、 硫代乙酸 以 吡啶 、 氯仿 为溶剂， 反应 48.0h， 以89%的产率得到benzyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  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