5-azido-3-oxapentyl 3-O-{(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonate)-3-O-(β-D-galactopyranosyl)}-2-acetamido-2-deoxy-α-D-galactopyranoside | 1023914-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-3-oxapentyl 3-O-{(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonate)-3-O-(β-D-galactopyranosyl)}-2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: (2S,4S,5R,6R)-5-acetamido-2-[(2R,3R,4S,5S,6R)-2-[(2S,3R,4R,5R,6R)-3-acetamido-2-[2-(2-azidoethoxy)ethoxy]-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 1023914-38-6
• 化学式: C₂₉H₄₉N₅O₂₀
• 分子量: 787.73
• InChiKey: PAJYESINCCEMPL-JJQVOTESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  357
• 氢给体数：
  12
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  5-azido-3-oxapentyl 3-O-{(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonate)-3-O-(β-D-galactopyranosyl)}-2-acetamido-2-deoxy-α-D-galactopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以95%的产率得到5-amino-3-oxapentyl 3-O-{(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonate)-3-O-(β-D-galactopyranosyl)}-2-acetamido-2-deoxy-α-D-galactopyranoside
  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：

  4-硝基苯基-D-吡喃葡糖苷 在 bovine β-galactosidase 、 pork liver α-(2->3) sialyltransferase 作用下， 以 phosphate buffer 为溶剂， 反应 84.0h， 生成 5-azido-3-oxapentyl 3-O-{(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonate)-3-O-(β-D-galactopyranosyl)}-2-acetamido-2-deoxy-α-D-galactopyranoside
  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

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.