8-methoxycarbonyloctyl 3-O-[2-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl]-α-D-glucopyranoside | 161453-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methoxycarbonyloctyl 3-O-[2-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl]-α-D-glucopyranoside
• 英文别名: methyl 9-[(2S,3R,4S,5R,6R)-4-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynonanoate
• CAS: 161453-84-5
• 化学式: C₂₈H₅₀O₁₈
• 分子量: 674.694
• InChiKey: KPBKKRDJWGXJIF-GWYBXCOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  284
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl 3-O-[2-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl]-α-D-glucopyranoside 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 3-O-[2-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl]-2-O-benzyl-4,6-O-p-methoxy-benzylidene-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以89%的产率得到8-methoxycarbonyloctyl 3-O-[2-O-(α-D-glucopyranosyl)-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 $g(a)-D-Glcp-(1-2)-$g(a)-D-Glcp-(1-3)-$g(a)-D-Glcp-ANALOGUES
  申请人：ALBERTA RESEARCH COUNCIL

  公开号：EP0837867A1

  公开（公告）日：1998-04-29
• 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
• [EN] MODIFIED alpha -D-Glcp-(1-2)- alpha -D-Glcp-(1-3)- alpha -D-Glcp-ANALOGUES<br/>[FR] alpha -D-Glcp-(1-2)- alpha -D-Glcp-(1-3)- alpha -D-Glcp-ANALOGUES MODIFIES
  申请人：ALBERTA RESEARCH COUNCIL

  公开号：WO1996040700A1

  公开（公告）日：1996-12-19

  (EN) Human immunodeficiency viruses (HIV-1 and HIV-2) are known to be the etiological agents of acquired immunodeficiency syndrome (AIDS). The carbohydrate structures on the virus coat proteins, gp120, are necessary for cell-cell fusion. The oligosaccharides on gp120 are processed by the enzyme glycosidase. The trisaccharide, $g(a)-D-Glcp-(1-2)-$g(a)-D-Glcp-(1-3)-$g(a)-D-GlcpO(CH2)8COOMe and its analogues modified at its terminal glucose residues are recognized by the enzyme and can inhibit glycosylation.(FR) On sait que les virus de l'immunodéficience humaine (VIH-1 et VIH-2) sont des agents étiologiques du syndrome d'immunodéficience acquise (SIDA). Les structures glucide situées sur les protéines de coque de virus, les gp120, sont nécessaires pour la fusion cellule-cellule. Les oligosaccharides situés sur les gp120 sont remaniés par l'enzyme glycosidase. Le trisaccharide, $g(a)-D-Glcp-(1-2)-$g(a)-D-Glcp-(1-3)-$g(a)-D-GlcpO(CH2)8COOMe et ses analogues modifiés au niveau des ses résidus glucose terminaux sont reconnus par l'enzyme et peuvent inhiber la glycosylation.
• 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.