| 1040147-65-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 1040147-65-6
• 化学式: C₃₆H₄₄O₇
• 分子量: 588.741
• InChiKey: VIDRAPXWCQJNSE-DKQOGILZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  43.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  A set of phosphatase-inert “molecular rulers” to probe for bivalent mannose 6-phosphate ligand–receptor interactions

  摘要：

  A set of bivalent mannose 6-phosphonate 'molecular rulers' has been synthesized to examine ligand binding to the M6P/IGF2R. The set is estimated to span a P-P distance range of 16-26 angstrom ( MMFF energy minimization on the hydrated phosphonates). Key synthetic transformations include sugar triflate displacement for phosphonate installation and Grubbs I cross-metathesis to achieve bivalency. Relative binding affinities were tested by radioligand displacement assays versus PMP-BSA ( pentamannosyl phosphate-bovine serum albumin). These compounds exhibit slightly higher binding affinities for the receptor (IC50's = 3.7-5 mu M) than the parent, monomeric mannose 6-phosphonate ligand and M6P itself (IC50 = 11.5 +/- 2.5 mu M). These results suggest that the use of an alpha-configured anomeric alkane tether is acceptable, as no significant thermodynamic penalty is apparently paid with this design. On the other hand, the modest gains in binding affinity observed suggest that this ligand set has not yet found true bivalent interaction with the M6P/IGF2R (i.e., simultaneous binding to two distinct M6P-binding pockets). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.094
• 作为产物：
  描述：

  1,6-二-O-乙酰基-2,3,4-三-O-苄基-α-D-吡喃甘露糖 、 6-庚烯-1-醇 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  A set of phosphatase-inert “molecular rulers” to probe for bivalent mannose 6-phosphate ligand–receptor interactions

  摘要：

  A set of bivalent mannose 6-phosphonate 'molecular rulers' has been synthesized to examine ligand binding to the M6P/IGF2R. The set is estimated to span a P-P distance range of 16-26 angstrom ( MMFF energy minimization on the hydrated phosphonates). Key synthetic transformations include sugar triflate displacement for phosphonate installation and Grubbs I cross-metathesis to achieve bivalency. Relative binding affinities were tested by radioligand displacement assays versus PMP-BSA ( pentamannosyl phosphate-bovine serum albumin). These compounds exhibit slightly higher binding affinities for the receptor (IC50's = 3.7-5 mu M) than the parent, monomeric mannose 6-phosphonate ligand and M6P itself (IC50 = 11.5 +/- 2.5 mu M). These results suggest that the use of an alpha-configured anomeric alkane tether is acceptable, as no significant thermodynamic penalty is apparently paid with this design. On the other hand, the modest gains in binding affinity observed suggest that this ligand set has not yet found true bivalent interaction with the M6P/IGF2R (i.e., simultaneous binding to two distinct M6P-binding pockets). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.094