8-methoxycarbonyloctyl 2-deoxy-β-D-lyxo-hexopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside | 98807-73-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methoxycarbonyloctyl 2-deoxy-β-D-lyxo-hexopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-3-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside
• CAS: 98807-73-9
• 化学式: C₂₄H₄₃NO₁₂
• 分子量: 537.605
• InChiKey: PBEMDYKUSZYKOY-CHKKKKDTSA-N

物化性质

• 沸点：
  775.7±60.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  37.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  193.47
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  8-methoxycarbonyoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(3,4,6-tri-O-benzyl-2-O-phenoxythiocarbonyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 palladium on activated charcoal 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 氢气 、 三正丁基氢锡 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 25.0~80.0 ℃ 、709.27 kPa 条件下， 反应 62.0h， 生成 8-methoxycarbonyloctyl 2-deoxy-β-D-lyxo-hexopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  乳酸-N-二糖I和N-乙酰-乳糖胺的单脱氧衍生物的合成，可作为区分α-1-岩藻糖基转移酶的底物

  摘要：

  摘要β-d -Gal-（1→3）-4-deoxy-β-d-GlcNAcOR和β-d -Gal-（1→4）-3-deoxy-β-d-GlcNAcOR的化学合成，其中报告了R =（CH2）8COOMe和Me。此外，2-deoxy-β-d-Gal-（1→3）-β-d-GlcNAcO（CH2）8COOMe和2-deoxy-β-d-Gal-（1→4）-β-d-GlcNAcO（合成CH 2）8 COOMe。关于这些化合物作为β-d-Gal-和β-d-GlcNAc-α-1-岩藻糖基转移酶的受体的行为，报道了来自其他实验室的初步结果。建议这些酶以其最有利的构象接受底物，并且该结合涉及极性和非极性相互作用，并具有在被取代的羟基附近的形貌特征。似乎取决于转移酶，识别可以包括或可以不包括两个糖单元。

  DOI：

  10.1016/0008-6215(85)85204-6

文献信息

• Recognition of β-d-Gal p-(1 → 3)-β-d-Glc pNAc-OR acceptor analogues by the Lewis α-(1 → 34)-fucosyltransferase from human milk
  作者：Minghui Du、Ole Hindsgaul

  DOI：10.1016/0008-6215(96)00047-x

  日期：1996.6

  The Lewis alpha-(1 --> 3/4)-frucosyltransferase (E.C. 2.4.1.65) transfers L-fucose from GDP-fucose to OH-4 of the Glc pNAc residue in the disaccharide beta-D-Gal p-(1 --> 3)-beta-D-Glc pNAc-OR [R = (CH2)(8)COOMe] (1) to give the Lewis-A blood group determinant beta-D-Gal p-(1 --> 3)-[alpha-L-Fuc p-(1 --> 4)]-beta-D-Glc pNAc-OR. Five deoxy analogues of 1, as well as its N-propionyl derivative, were chemically synthesized and kinetically evaluated as both substrates and inhibitors for the enzyme from human milk. The unmodified acceptor 1 had K-m = 640 mu M with V-max set arbitrarily to 100. The 6-deoxy (K-m = 400 mu M, V-max = 90) and N-propionyl compounds (K-m = 330 mu M, V-max = 170) remained excellent substrates while the 4-deoxy compound was a very weak competitive inhibitor with K-i = 9 mM. Deoxygenation of OH-2' and OH-4' (of the Gal residue) in 1 had little effect on the activity. The OH-6 group of the Gal residue proved to be critical for recognition by the enzyme since substitution of this group with hydrogen led to an inactive compound. (C) 1996 Elsevier Science Ltd.