bis-1,11-[2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl]-(6-tosyl-3,9-dioxa-6-aza-undecane) | 244267-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis-1,11-[2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl]-(6-tosyl-3,9-dioxa-6-aza-undecane)
• CAS: 244267-48-9
• 化学式: C₅₉H₇₁N₃O₁₆S
• 分子量: 1110.29
• InChiKey: DHGCJMBZIPEVBX-XZFCNASISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  79.0
• 可旋转键数：
  26.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  206.34
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  bis-1,11-[2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl]-(6-tosyl-3,9-dioxa-6-aza-undecane) 在 palladium on activated charcoal bovine β-galactosidase 、 氢气 作用下， 以 甲醇 、 phosphate buffer 为溶剂， 反应 168.0h， 生成 bis-1,11-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]-(6-tosyl-3,9-dioxa-6-aza-undecane)
  参考文献：
  名称：

  Chemoenzymatic synthesis of spacer-linked oligosaccharides for the preparation of neoglycoproteins

  摘要：

  In the present work, the combination of chemical and enzymatic methods to obtain neoglycoproteins is described. Three bovine serum albumin (BSA)-conjugates, BSA-[GalNAc alpha-], BSA-[Gal(beta 1-3)GalNAc(alpha-], and BSA-[Neu5Ac(alpha 2-3)Gal(beta 1-3)GalNAc(alpha-], were prepared, alpha GalNAc derivatives were galactosylated employing crude P-galactosidase from bovine testes. The use of oversaturated donor solutions (pNP beta Gal) enhanced the yields up to 60%. This method was verified using divalent structures as accepters, that rendered di- and tri-galactosylated products. Further treatment of the disaccharides with CMP-Neu5Ac and alpha 2-3 sialyltransferase from pork liver led to formation of trisaccharides. Finally, mono-, di-, and trisaccharides were coupled to BSA employing a thiolic group introduced into the protein for Michael addition to a maleinimide group in the spacer-ann of the saccharide components. The results were monitored by HPLC and MALDI-TOF. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00073-7
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 calcium sulfate 、 barium dihydroxide 、 sodium methylate 、 氰化汞 、 对甲苯磺酸 、 barium(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 130.0h， 生成 bis-1,11-[2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl]-(6-tosyl-3,9-dioxa-6-aza-undecane)
  参考文献：
  名称：

  Chemoenzymatic synthesis of spacer-linked oligosaccharides for the preparation of neoglycoproteins

  摘要：

  In the present work, the combination of chemical and enzymatic methods to obtain neoglycoproteins is described. Three bovine serum albumin (BSA)-conjugates, BSA-[GalNAc alpha-], BSA-[Gal(beta 1-3)GalNAc(alpha-], and BSA-[Neu5Ac(alpha 2-3)Gal(beta 1-3)GalNAc(alpha-], were prepared, alpha GalNAc derivatives were galactosylated employing crude P-galactosidase from bovine testes. The use of oversaturated donor solutions (pNP beta Gal) enhanced the yields up to 60%. This method was verified using divalent structures as accepters, that rendered di- and tri-galactosylated products. Further treatment of the disaccharides with CMP-Neu5Ac and alpha 2-3 sialyltransferase from pork liver led to formation of trisaccharides. Finally, mono-, di-, and trisaccharides were coupled to BSA employing a thiolic group introduced into the protein for Michael addition to a maleinimide group in the spacer-ann of the saccharide components. The results were monitored by HPLC and MALDI-TOF. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00073-7