8-methoxycarbonyloctyl 2-acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside | 82993-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: 8-(Methoxycarbonyl)octyl 2-(acetylamino)-3-O-(6-deoxy-alpha-L-galactopyranosyl)-4-O-beta-D-galactopyranosyl-2-deoxy-beta-D-glucopyranoside；methyl 9-[(2R,3R,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxynonanoate
• CAS: 82993-39-3
• 化学式: C₃₀H₅₃NO₁₇
• 分子量: 699.747
• InChiKey: WACAMKYYEIIMEH-JAXMHQHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  273
• 氢给体数：
  9
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 palladium dihydroxide 草酰溴 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.5h， 生成 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Rapid Chemical Synthesis of Sugar Nucleotides in a Form Suitable for Enzymic Oligosaccharide Synthesis

  摘要：

  DOI：

  10.1021/jo00106a007

文献信息

• Synthesis of type 2 human blood-group antigenic determinants. The H, X, and Y haptens and variations of the H type 2 determinant as probes for the combining site of the lectin I of Ulex europaeus
  作者：Ole Hindsgaul、Thomas Norberg、Jacques Le Pendu、Raymond U. Lemieux

  DOI：10.1016/0008-6215(82)84034-2

  日期：1982.11

  Chemical syntheses of the human blood-group antigenic determinants derived from N-acetyllactosamine are described; namely, the 6-deoxy derivative, the 4'-epimer, and the 5 H type 2 [alpha LFuc(1 to 2)beta DGal-(1 to 4)beta DGlcNAc], X [beta DGal(1 to 4)[alpha LFuc(1 to 3)[beta DGlcNAc], and Y [alpha LFuc-(1 to 2)beta DGal(1 to 4)[alpha LFuc(1 to 3)]beta DGlcNAc] determinants as glycosides of 8-carboxymethyloctanol

  描述了衍生自N-乙酰基乳糖胺的人血型抗原决定簇的化学合成。即6-脱氧衍生物，4'-末端和5 H 2型[αLFuc（1至2）beta DGal-（1至4）beta DGlcNAc]，X [beta DGal（1至4）[ αLFuc（1至3）βDGlcNAc和Y [αLFuc-（1至2）βDGal（1至4）[αLFuc（1至3）]βDGlcNAc]决定基为8-羧甲基辛醇的糖苷。为了研究H 2决定簇与欧洲油菜的凝集素I的结合，还设计了专门改变H 2决定簇的亲水和疏水部分的结构。即6-脱氧衍生物，4'-末端和5“-正同源物。这些结构的使用，连同H 1型半抗原和H 1型和H 2型决定簇的N-去乙酰化形式一起，作为凝集素对O红细胞凝集的抑制剂，可以得出以下结论：H 2决定簇的结合是疏水性 结合涉及行列式分子的楔形部分，该楔形部分基本上是疏水性的，除了在楔形尖端处的5-羟甲基基团外，与O-5形成分子内氢
• Novel Hybrid Morpholino-Glycopeptides with the Amino Acid Nitrogen Replacing C-3 of the Pyranose Ring
  作者：Minghui Du、Ole Hindsgaul

  DOI：10.1055/s-1997-800

  日期：1997.4

  Periodate oxidation of glycopyranosides yields dialdehydes that can be reductively aminated in the presence of amino acids to produce hybrid glycopeptides where the amino acid nitrogen is inserted into the resulting 2,4-dideoxypyranoside at position 3. Nine such 3-morpholino derivatives were prepared, including a disaccharide analog of N-acetyllactosamine (β-Gal(1→4)βGlcNAc) where the nitrogen of glycine was inserted into the galactose ring. The resulting hybrid disaccharide was an excellent substrate for a mild fucosyltransferase which converted it to a novel functionalized LeX mimic.

  高碘酸氧化吡喃糖苷可产生二醛，二醛可在氨基酸存在下进行还原性胺化，生成杂化糖肽，其中氨基酸氮插入生成的 2,4-二脱氧吡喃糖苷的第 3 位。我们制备了九种这样的 3-吗啉衍生物，包括一种 N-乙酰半乳糖胺的二糖类似物（δ²-Gal(1→4)δGlcNAc），其中甘氨酸的氮被插入半乳糖环中。由此产生的杂交二糖是一种温和的岩藻糖基转移酶的极佳底物，这种酶可将其转化为一种新型的功能化 LeX 模拟物。
• Acceptor Specificity of Different Length Constructs of Human Recombinant α1,3/4-Fucosyltransferases
  作者：Theodora de Vries、Cheryl A. Srnka、Monica M. Palcic、Stuart J. Swiedler、Dirk H. van den Eijnden、Bruce A. Macher

  DOI：10.1074/jbc.270.15.8712

  日期：1995.4

  activity toward glycoproteins, whereas chimeric Fuc-TIII and Fuc-TV had a decreased activity with glycosphingolipids, compared to the full-length enzymes. Unexpectedly, chimeric Fuc-TV exhibited a GDP-fucose hydrolyzing activity. In substrates with multiple acceptor sites, the preferred site of fucosylation was identified. Fuc-TIII and Fuc-TV catalyzed fucose transfer exclusively to OH-3 of glucose in

  在COS-7细胞中表达的重组全长，与膜结合的岩藻糖基转移酶的受体特异性以及α1,3-岩藻糖基转移酶（Fuc-T）III，Fuc-TIV和Fuc-的可溶性蛋白A嵌合形式电视被分析为各种寡糖，糖脂和糖蛋白底物。我们对全长酶的研究结果证实并扩展了先前的研究。然而，与全长酶相比，嵌合Fuc-Ts对糖蛋白的活性增加，而嵌合Fuc-TIII和Fuc-TV对糖鞘脂的活性却降低。出乎意料的是，嵌合的Fuc-TV表现出GDP-岩藻糖的水解活性。在具有多个受体位点的底物中，鉴定了岩藻糖基化的优选位点。1 H NMR光谱证实，Fuc-TIII和Fuc-TV分别催化将岩藻糖仅转移至乳糖N-新四糖和乳糖N-四糖中葡萄糖的OH-3上。薄层色谱免疫染色显示，FucT-IV首选nLc6Cer中的远端GlcNAc残基，而Fuc-TV则首选近端G1-cNAc残基。将Fuc-TIV或Fuc-TV与VI3NeuAcnLc6Cer
• Enzymatic fucosylations with purine-diphosphate-fucoses (PDP-Fucoses)
  作者：Gabi Baisch、Reinhold Öhrlein、Andreas Katopodis

  DOI：10.1016/s0960-894x(96)00543-4

  日期：1996.12

  Two cloned fucosyltransferases, Fuc-t III and Fuc-t VI, are probed on a preparative scale with non-natural donor-substrates, in which the guanosine of the natural donor guanosine diphosphate-fucose is replaced by other purines, Surprisingly, the novel purine-diphosphate-fucoses (PDP-Fuc) are recognized by both enzymes as donor-substrates. Copyright (C) 1996 Elsevier Science Ltd
• US5874411A
  申请人：——

  公开号：US5874411A

  公开（公告）日：1999-02-23