undecaprenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-acetyl-α-D-galactopyranosyl-(1->3)-2,4-diacetamido-2,4,6-trideoxy-α-D-glucopyranosyl diphosphate | 1186313-76-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: undecaprenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-acetyl-α-D-galactopyranosyl-(1->3)-2,4-diacetamido-2,4,6-trideoxy-α-D-glucopyranosyl diphosphate
• CAS: 1186313-76-7
• 化学式: C₉₁H₁₄₄N₄O₂₆P₂
• 分子量: 1772.1
• InChiKey: UFPRFMVCTFAYDG-ZPJJLECPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.37
• 重原子数：
  123.0
• 可旋转键数：
  52.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  396.34
• 氢给体数：
  6.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  undecaprenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-acetyl-α-D-galactopyranosyl-(1->3)-2,4-diacetamido-2,4,6-trideoxy-α-D-glucopyranosyl diphosphate 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以79%的产率得到undecaprenyl 2-acetamido-2-deoxy-α-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-α-D-galactopyranosyl-(1->3)-2,4-diacetamido-2,4,6-trideoxy-α-D-glucopyranosyl diphosphate
  参考文献：
  名称：

  Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation

  摘要：

  Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E](3),[Z](7))-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl phosphate (Und-P). It was coupled with glycosyl phosphates to afford Und-PP-linked glycans, including core trisaccharide of Campylobacter jejuni N-glycan. Our synthetic method for Und-PP-linked glycan would provide various substrates as a useful tool for systematic analysis of bacterial protein N-glycosylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.032
• 作为产物：
  描述：

  2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-acetyl-α-D-galactopyranosyl-(1->3)-2,4-diacetamido-2,4,6-trideoxy-α-D-glucopyranosyl phosphate 、 disodium undecaprenyl phosphate 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 78.0h， 以67%的产率得到undecaprenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-3,6-di-O-acetyl-α-D-galactopyranosyl-(1->3)-2,4-diacetamido-2,4,6-trideoxy-α-D-glucopyranosyl diphosphate
  参考文献：
  名称：

  Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation

  摘要：

  Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E](3),[Z](7))-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl phosphate (Und-P). It was coupled with glycosyl phosphates to afford Und-PP-linked glycans, including core trisaccharide of Campylobacter jejuni N-glycan. Our synthetic method for Und-PP-linked glycan would provide various substrates as a useful tool for systematic analysis of bacterial protein N-glycosylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.032