8-Methoxycarbonyloctyl 2-O-benzyl-4,6-O-p-methoxy-benzylidene-3-O-(2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside | 161453-81-2

• 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: 8-Methoxycarbonyloctyl 2-O-benzyl-4,6-O-p-methoxy-benzylidene-3-O-(2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside
• 英文别名: methyl 9-[[(4aR,6S,7R,8S,8aR)-8-[(2R,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-prop-2-enoxyoxan-2-yl]oxy-2-(4-methoxyphenyl)-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]nonanoate
• CAS: 161453-81-2
• 化学式: C₆₁H₇₄O₁₄
• 分子量: 1031.25
• InChiKey: GDXFKFLIHSAZSZ-KDURLJBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  75
• 可旋转键数：
  31
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  8-Methoxycarbonyloctyl 2-O-benzyl-4,6-O-p-methoxy-benzylidene-3-O-(2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 在 Wilkinson's catalyst 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 乙醇 、 水 、 丙酮 、 苯 为溶剂， 反应 24.75h， 生成 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
  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：

  4-甲氧基苯甲醛二甲缩醛 在 四乙基溴化铵 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 73.0h， 生成 8-Methoxycarbonyloctyl 2-O-benzyl-4,6-O-p-methoxy-benzylidene-3-O-(2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside
  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

文献信息

• MODIFIED ALPHA-D-Glcp-(1-2)-ALPHA-D-Glcp-(1-3)-ALPHA-D-Glcp-ANALOGUES
  申请人：ALBERTA RESEARCH COUNCIL

  公开号：EP0837867B1

  公开（公告）日：2001-08-16
• US5929037A
  申请人：——

  公开号：US5929037A

  公开（公告）日：1999-07-27
• 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
  作者：Christine H. Scaman、Ole Hindsgaul、Monica M. Palcic、Om P. Srivastava

  DOI：10.1016/s0008-6215(96)00242-x

  日期：1996.12

  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.