5-chloro-3-oxapentyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 244267-45-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-3-oxapentyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 2-(2-chloroethoxy)ethyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-2-[2-(2-chloroethoxy)ethoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 244267-45-6
• 化学式: C₁₂H₂₂ClNO₇
• 分子量: 327.762
• InChiKey: WFEKKWDRJPGTBV-LZQZFOIKSA-N

物化性质

• 沸点：
  601.9±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-chloro-3-oxapentyl 2-acetamido-2-deoxy-β-D-glucopyranoside 在 barium dihydroxide 、 对甲苯磺酸 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 5-chloro-3-oxapentyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  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 、 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 5-chloro-3-oxapentyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  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.