ethyl [methyl (E)-2,3,4-tri-O-trimethylsilyl-6,7-dideoxy-α-D-manno-oct-6-enopyranoside]uronate | 503274-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl [methyl (E)-2,3,4-tri-O-trimethylsilyl-6,7-dideoxy-α-D-manno-oct-6-enopyranoside]uronate
• CAS: 503274-39-3
• 化学式: C₂₀H₄₂O₇Si₃
• 分子量: 478.806
• InChiKey: MGMKHONRPLPJHU-PBBMDTBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  ethyl [methyl (E)-2,3,4-tri-O-trimethylsilyl-6,7-dideoxy-α-D-manno-oct-6-enopyranoside]uronate 在 palladium on activated charcoal sodium hydroxide 、 ammonium cerium(IV) nitrate 、 水 、 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.33h， 生成 sodium (methyl 6,7-dideoxy-α-D-manno-octopyranoside)uronate
  参考文献：
  名称：

  Synthesis and receptor binding affinity of carboxylate analogues of the mannose 6-phosphate recognition marker

  摘要：

  The mannose 6-phosphate/insulin-like growth factor II receptor (M6P/IGF2R) is involved in multiple physiological pathways including targeting of lysosomal enzymes, degradation of IGF2, and cicatrization through TGF beta activation. To target potential therapeutics to this membrane receptor, four carboxylate analogues of mannose 6-phosphate (M6P) were synthesized. Three of them, two isosteric carboxylate analogues and a malonate derivative, showed a binding affinity for the M6P/IGF2R equivalent to or higher than that of M6P. Contrary to M6P, all these analogues were particularly stable in human serum. Moreover, these derivatives did not present any cytotoxic activity against two human cell lines. These analogues represent a new potential for the lysosomal targeting of enzyme replacement therapy in lysosomal diseases or to prevent the membrane-associated activities of the M6P/IGF2R. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.024
• 作为产物：
  描述：

  methyl 2,3,4,6-tetrakis-O-(trimethylsilyl)-α-D-mannopyranoside 在 吡啶 、 chromium(VI) oxide 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 ethyl [methyl (E)-2,3,4-tri-O-trimethylsilyl-6,7-dideoxy-α-D-manno-oct-6-enopyranoside]uronate
  参考文献：
  名称：

  Synthesis and receptor binding affinity of carboxylate analogues of the mannose 6-phosphate recognition marker

  摘要：

  The mannose 6-phosphate/insulin-like growth factor II receptor (M6P/IGF2R) is involved in multiple physiological pathways including targeting of lysosomal enzymes, degradation of IGF2, and cicatrization through TGF beta activation. To target potential therapeutics to this membrane receptor, four carboxylate analogues of mannose 6-phosphate (M6P) were synthesized. Three of them, two isosteric carboxylate analogues and a malonate derivative, showed a binding affinity for the M6P/IGF2R equivalent to or higher than that of M6P. Contrary to M6P, all these analogues were particularly stable in human serum. Moreover, these derivatives did not present any cytotoxic activity against two human cell lines. These analogues represent a new potential for the lysosomal targeting of enzyme replacement therapy in lysosomal diseases or to prevent the membrane-associated activities of the M6P/IGF2R. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.01.024

文献信息

• Synthesis and biological evaluation of new mannose 6-phosphate analogues
  作者：Sébastien Vidal、Marcel Garcia、Jean-Louis Montero、Alain Morère

  DOI：10.1016/s0968-0896(02)00264-x

  日期：2002.12

  Three new analogues of mannose 6-phosphate (M6P)-a sulphate and two carboxylates-have been synthesized and their affinity toward the M6P/IGFII receptor evaluated by affinity column chromatography. These compounds display strong binding to the receptor and therefore are new M6P analogues which may find some dermatological applications. for example healing of post-surgical scars. (C) 2002 Elsevier Science Ltd. All rights reserved.