p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside | 81562-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside
• CAS: 81562-03-0
• 化学式: C₃₂H₃₉NO₂₀
• 分子量: 757.656
• InChiKey: FPUPORSBEXGRKK-AARGFYGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  53.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  264.16
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为产物：
  描述：

  p-nitrophenyl 2,6-di-O-acetyl-3,4-O-isopopylidene-β-D-galactopyranoside 在 水 、 氰化汞 、 对甲苯磺酸 、 溶剂黄146 、 三氟乙酸 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 7.33h， 生成 p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  对硝基苯基3-O-β-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷和对硝基苯基3-O-α-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷

  摘要：

  摘要对硝基苯基2,4,6-三-O-乙酰基-β-d-吡喃半乳糖苷（2）与2,3,4,6-四-O-乙酰基-α-d的糖基化反应（氰化汞催化）在乙腈中的-半乳糖基吡喃糖基溴化物以几乎相等的比例提供α-（1→3）-和β-（1→3）连接的二糖七乙酸酯（分别为4和6）。对-硝基苯基2-O-苯甲酰基-4,6-O-亚苄基-β-d-吡喃半乳糖苷（3）的类似糖基化反应产生了β-（1→3）-和α-（1→3）-相连，以3：1的比例完全保护的二糖衍生物（分别为8和10）。4，6，8和10的结构由它们各自的1 Hn.mr光谱证明。4和6的O-脱乙酰基分别提供对-硝基苯基3- O-α-d-吡喃半乳糖基-β-d-吡喃半乳糖苷（5）和对-硝基苯基3- O-β-d-吡喃半乳糖基-β-d-半乳糖吡喃糖苷（7）。8和10的O-脱酰作用提供了二糖衍生物（9和11）。9和11的亚苄基的切割分别给出了二糖7和5。5，7，9和11的结构是通过13

  DOI：

  10.1016/s0008-6215(00)81003-4

文献信息

• Chemoenzymatic synthesis of spacer-linked oligosaccharides for the preparation of neoglycoproteins
  作者：Raul Gonzalez Lio、Joachim Thiem

  DOI：10.1016/s0008-6215(99)00073-7

  日期：1999.4

  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.