1,2-dipalmitoyl-3-(N-palmitoyl-6'-amino-6'-deoxy-β-D-glucopyranosyl)-sn-glycerol | 1428256-88-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-dipalmitoyl-3-(N-palmitoyl-6'-amino-6'-deoxy-β-D-glucopyranosyl)-sn-glycerol
• 英文别名: [(2S)-3-[(2R,3R,4S,5S,6R)-6-[(hexadecanoylamino)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-hexadecanoyloxypropyl] hexadecanoate
• CAS: 1428256-88-5
• 化学式: C₅₇H₁₀₉NO₁₀
• 分子量: 968.493
• InChiKey: FQQGDOIXTUYSNI-PJVCNUQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.8
• 重原子数：
  68
• 可旋转键数：
  52
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  甲基-6-O-三苯基甲基-alpha-D-吡喃葡萄糖苷 在 sodium azide 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 三氟化硼乙醚 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 palladium(II) hydroxide 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， -20.0~123.0 ℃ 、2.0 MPa 条件下， 反应 118.5h， 生成 1,2-dipalmitoyl-3-(N-palmitoyl-6'-amino-6'-deoxy-β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay

  摘要：

  In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.007

文献信息

• Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay
  作者：Alexander Rohe、Christiane Göllner、Kanin Wichapong、Frank Erdmann、Ghassab M.A. Al-Mazaideh、Wolfgang Sippl、Matthias Schmidt

  DOI：10.1016/j.ejmech.2012.06.007

  日期：2013.3

  In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site. (C) 2012 Elsevier Masson SAS. All rights reserved.