2-(trimethylsilyl)ethyl [5-(5-acetamido-3,5-dideoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)oxyacetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid]-(2→3)-(β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside | 1159257-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl [5-(5-acetamido-3,5-dideoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)oxyacetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid]-(2→3)-(β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside
• 英文别名: 2-(trimethylsilyl)ethyl 5-acetamido-8-O-methyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2->11)-3,5-dideoxy-5-glycolylamido-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• CAS: 1159257-92-7
• 化学式: C₄₀H₇₀N₂O₂₈Si
• 分子量: 1055.08
• InChiKey: CTGLOXJJLWXQLI-OVMSBYTRSA-N

物化性质

• 沸点：
  1340.3±65.0 °C(predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以31 mg的产率得到2-(trimethylsilyl)ethyl [5-(5-acetamido-3,5-dideoxy-8-O-methyl-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)oxyacetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid]-(2→3)-(β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the starfish ganglioside LLG-3 tetrasaccharide

  摘要：

  The first synthesis of the ganglioside LLG-3 tetrasaccharide, which has attractive biological activities as well as a unique structure, is described. A C8-methoxy decorated sialic acid building block was initially prepared and a glycolic acid moiety was then introduced by sialylation. Amide condensation between the sialyl glycolic acid and an amino group at C5 on the sialyllactoside unit afforded the fully protected LLG-3 tetrasaccharide. Finally, the desired tetrasaccharide part of LLG-3 was obtained after careful global deprotection.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.003

文献信息

• Structure-Activity Relationship Study of the Neuritogenic Potential of the Glycan of Starfish Ganglioside LLG-3 ‡
  作者：Megumi Yamagishi、Ritsuko Hosoda-Yabe、Hideki Tamai、Miku Konishi、Akihiro Imamura、Hideharu Ishida、Tomio Yabe、Hiromune Ando、Makoto Kiso

  DOI：10.3390/md13127062

  日期：——

  LLG-3 is a ganglioside isolated from the starfish Linchia laevigata. To clarify the structure-activity relationship of the glycan of LLG-3 toward rat pheochromocytoma PC12 cells in the presence of nerve growth factor, a series of mono- to tetrasaccharide glycan derivatives were chemically synthesized and evaluated in vitro. The methyl group at C8 of the terminal sialic acid residue was crucial for

  LLG-3是从海星Linchia laevigata中分离出来的神经节苷脂。为了阐明在神经生长因子存在下LLG-3聚糖对大鼠嗜铬细胞瘤PC12细胞的构效关系，化学合成了一系列单糖至四糖聚糖衍生物，并在体外进行了评估。末端唾液酸残基C8处的甲基对于神经形成活性至关重要，而末端三糖部分是最小的活性基序。此外，三糖还通过有丝分裂原激活的蛋白激酶（MAPK）信号传导刺激人神经母细胞瘤SH-SY5Y细胞中的神经形成。加入1或10 nM三糖可迅速诱导细胞外信号调节激酶（ERK）1/2的磷酸化。刺激后5分钟，磷酸化ERK与ERK的比例达到最大值，然后逐渐下降。但是，三糖不会诱导明显的Akt磷酸化。这些作用通过用MAPK抑制剂U0126进行预处理而消除，该抑制剂可抑制酶MEK1和MEK2。此外，U0126剂量依赖性地响应于三糖而抑制ERK 1/2的磷酸化。因此，我们得出结论，三糖通过MAPK / ERK信