3-N-acryloylaminopropyl-3,4,6-tri-O-acetyl-2-O-(methyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-D-galactopyranoside | 1616792-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-N-acryloylaminopropyl-3,4,6-tri-O-acetyl-2-O-(methyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-D-galactopyranoside
• CAS: 1616792-64-3
• 化学式: C₃₀H₄₃NO₁₇
• 分子量: 689.668
• InChiKey: PLMRFTDBYCITBW-YQMWSOOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.23
• 重原子数：
  48.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  223.82
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  3-N-acryloylaminopropyl-3,4,6-tri-O-acetyl-2-O-(methyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到3-N-acryloyl-aminopropyl-2-O-(α-L-fucopyranosyl)-D-galactopyranoside
  参考文献：
  名称：

  Photoactivatable Glycopolymers for the Proteome-Wide Identification of Fucose-α(1-2)-Galactose Binding Proteins

  摘要：

  Although fucose-alpha(1-2)-galactose (Fuc alpha(1-2)Gal)-containing glycans have been implicated in cognitive processes such as learning and memory, their precise molecular mechanisms are poorly understood. Here we employed the use of multivalent glycopolymers to enable the first proteome-wide identification of weak affinity, low abundance Fuc alpha(1-2)Gal glycan-binding proteins (GBPs). Biotin-terminated glycopolymers containing photoactivatable cross-linking groups were designed to capture and enrich GBPs from rat brain lysates. Candidate proteins were tested for their ability to bind Fuc alpha(1-2)Gal, and the functional significance of the interaction was investigated for the synaptic vesicle protein SV2a using a knockout mouse system. The results suggest a role for SV2a-Fuc alpha(1-2)Gal interactions in SV2a trafficking and synaptic vesicle recycling. More broadly, our studies outline a general chemical approach for the systems-level discovery of novel GBPs.

  DOI：

  10.1021/ja502482a
• 作为产物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-O-(methyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-1-thio-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 palladium carbon (20 wt%) 、 氢气 、 碳酸氢钠 、 三乙胺 作用下， 以 水 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 4.75h， 生成 3-N-acryloylaminopropyl-3,4,6-tri-O-acetyl-2-O-(methyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-D-galactopyranoside
  参考文献：
  名称：

  Photoactivatable Glycopolymers for the Proteome-Wide Identification of Fucose-α(1-2)-Galactose Binding Proteins

  摘要：

  Although fucose-alpha(1-2)-galactose (Fuc alpha(1-2)Gal)-containing glycans have been implicated in cognitive processes such as learning and memory, their precise molecular mechanisms are poorly understood. Here we employed the use of multivalent glycopolymers to enable the first proteome-wide identification of weak affinity, low abundance Fuc alpha(1-2)Gal glycan-binding proteins (GBPs). Biotin-terminated glycopolymers containing photoactivatable cross-linking groups were designed to capture and enrich GBPs from rat brain lysates. Candidate proteins were tested for their ability to bind Fuc alpha(1-2)Gal, and the functional significance of the interaction was investigated for the synaptic vesicle protein SV2a using a knockout mouse system. The results suggest a role for SV2a-Fuc alpha(1-2)Gal interactions in SV2a trafficking and synaptic vesicle recycling. More broadly, our studies outline a general chemical approach for the systems-level discovery of novel GBPs.

  DOI：

  10.1021/ja502482a