5-azido-3-oxapentyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside | 195531-59-0

• 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 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside
• 英文别名: 5-azido-3-oxa-pentyl-2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside；N-[(2S,3R,4R,5R,6R)-2-[2-(2-azidoethoxy)ethoxy]-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 195531-59-0
• 化学式: C₁₈H₃₂N₄O₁₂
• 分子量: 496.472
• InChiKey: RSAFLVPFHRMLRM-ZMHUMUBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  211
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5-azido-3-oxapentyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 N-[2-[2-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyethoxy]ethyl]-3-(2,5-dioxopyrrol-1-yl)propanamide
  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：

  3-oxa-5-O-tosyl-pentyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 甲醇 、 二环己烷并-18-冠醚-6 、 sodium azide 、 β-galactosidase from bovine testes 、 sodium phosphate-citrate buffer 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 丁酮 为溶剂， 反应 58.0h， 生成 5-azido-3-oxapentyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Galactosylation with β-galactosidase from bovine testes employing modified acceptor substrates

  摘要：

  In this study beta 1-3 linked analogues of the T-antigen determinant were sythesized in preparative scale by transgalactosylation using beta-galactosidase from bovine testes to give synthetic antigens. Accepters with modifications of the sugar residue such as alpha-glycosylated spacers, as well as GlcNAc-alpha OR- and 2dGal-alpha OR-substrates opened further possibilities for galactosylation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00071-0

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.
• Galactosylation with β-galactosidase from bovine testes employing modified acceptor substrates
  作者：Ulrike Gambert、Raul Gonzalez Lio、Erzsébet Farkas、Joachim Thiem、Vicente Verez Bencomo、András Lipták

  DOI：10.1016/s0968-0896(97)00071-0

  日期：1997.7

  In this study beta 1-3 linked analogues of the T-antigen determinant were sythesized in preparative scale by transgalactosylation using beta-galactosidase from bovine testes to give synthetic antigens. Accepters with modifications of the sugar residue such as alpha-glycosylated spacers, as well as GlcNAc-alpha OR- and 2dGal-alpha OR-substrates opened further possibilities for galactosylation. (C) 1997 Elsevier Science Ltd.