2'-azidoethyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside | 904926-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-azidoethyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• CAS: 904926-03-0
• 化学式: C₂₂H₃₈N₄O₁₅
• 分子量: 598.562
• InChiKey: RZDFJKWNPVAOOW-CPHDTMOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.07
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  295.08
• 氢给体数：
  9.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2'-azidoethyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 、 5`-二磷酸鸟嘌呤核苷-岩藻糖二钠盐 在 α-(1->3)-fucosyltransferase VI 、 sodium cacodylate 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 以47%的产率得到2'-azidoethyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Large-scale chemoenzymatic synthesis of blood group and tumor-associated poly-N-acetyllactosamine antigens

  摘要：

  Poly-N-acetyllactosamines (pLNs) are common terminal sugars of many N- and O-linked glycan structures present in glycoproteins and glycolipids. Utilizing various glycosyltransferases, we developed new and efficient chemoenzymatic methods for the synthesis of pLNs in gram-scale. Specifically, the use of sialyltransferases and fucosyltransferases enabled us to synthesize and purify 24 blood group and tumor-associated pLN derivatives with alpha-(2 -> 3)- and alpha-(2 -> 6)-linked sialic acid, as well as with alpha-(1 -> 2)- and alpha-(1 -> 3)-linked fucose. All synthesized derivatives were linked to a short 2-azidoethyl spacer for further modification. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.043
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 在 α-(1->2)-fucosyltransferase II 、 β-(1->4)-galactosyltransferase 、 UDP-galactose 4'-epimerase 、 sodium cacodylate 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 反应 72.0h， 生成 2'-azidoethyl α-L-fucopyranosyl-(1->2)-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Large-scale chemoenzymatic synthesis of blood group and tumor-associated poly-N-acetyllactosamine antigens

  摘要：

  Poly-N-acetyllactosamines (pLNs) are common terminal sugars of many N- and O-linked glycan structures present in glycoproteins and glycolipids. Utilizing various glycosyltransferases, we developed new and efficient chemoenzymatic methods for the synthesis of pLNs in gram-scale. Specifically, the use of sialyltransferases and fucosyltransferases enabled us to synthesize and purify 24 blood group and tumor-associated pLN derivatives with alpha-(2 -> 3)- and alpha-(2 -> 6)-linked sialic acid, as well as with alpha-(1 -> 2)- and alpha-(1 -> 3)-linked fucose. All synthesized derivatives were linked to a short 2-azidoethyl spacer for further modification. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.043