9-[(2S,3R,4S,5R,6R)-3,5-Dihydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester | 187729-29-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9-[(2S,3R,4S,5R,6R)-3,5-Dihydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
• CAS: 187729-29-9
• 化学式: C₂₂H₄₀O₁₃
• 分子量: 512.552
• InChiKey: DPPFTOHFHJFIMC-FIRLIKODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.47
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  204.83
• 氢给体数：
  7.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  9-[(2S,3R,4S,5R,6R)-3,5-Dihydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成
  参考文献：
  名称：

  Synthesis of α-d-Glcp-(1 → 2)-α-d-Glcp-(1 → 3)-α-d-Glcp-O-(CH2)8COOCH3 for use in the assay of α-glucosidase I activity

  摘要：

  The chemical synthesis of alpha-D-Glcp-(1 --> 2)-alpha-D-Glc p-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (9), a substrate specific for cr-glucosidase I, is reported. This enzyme removes the terminal alpha-D-Glcp unit to produce alpha-D-Glcp-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (10). This is the first synthetic substrate described for glucosidase I that allows kinetic evaluation of substrates and inhibitors of this enzyme. Tetramethylrhodamine was coupled to 9 through an ethylenediamine linker to produce a brilliant red derivative. Addition of this fluorescent dye did not affect enzyme binding to the substrate, as determined by a comparison of the K-m value (1.3 mM). The fluorescent label allows visual detection of 2-3 pmol of product by TLC. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00242-x
• 作为产物：
  描述：

  8-Methoxycarbonyloctyl 2-O-benzyl-4,6-O-p-methoxy-benzylidene-3-O-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以94%的产率得到9-[(2S,3R,4S,5R,6R)-3,5-Dihydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of α-d-Glcp-(1 → 2)-α-d-Glcp-(1 → 3)-α-d-Glcp-O-(CH2)8COOCH3 for use in the assay of α-glucosidase I activity

  摘要：

  The chemical synthesis of alpha-D-Glcp-(1 --> 2)-alpha-D-Glc p-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (9), a substrate specific for cr-glucosidase I, is reported. This enzyme removes the terminal alpha-D-Glcp unit to produce alpha-D-Glcp-(1 --> 3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 (10). This is the first synthetic substrate described for glucosidase I that allows kinetic evaluation of substrates and inhibitors of this enzyme. Tetramethylrhodamine was coupled to 9 through an ethylenediamine linker to produce a brilliant red derivative. Addition of this fluorescent dye did not affect enzyme binding to the substrate, as determined by a comparison of the K-m value (1.3 mM). The fluorescent label allows visual detection of 2-3 pmol of product by TLC. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00242-x