8-methoxycarbonyloctyl 2-acetamido-2-deoxy-4-O-(alpha-L-fucopyranosyl)-3-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside | 56343-02-3

• 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-4-O-(alpha-L-fucopyranosyl)-3-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside
• 英文别名: methyl 9-[(2R,3R,4R,5S,6R)-3-acetamido-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxynonanoate
• CAS: 56343-02-3
• 化学式: C₃₀H₅₃NO₁₇
• 分子量: 699.747
• InChiKey: RAWIMSUPKCBBKH-JAXMHQHXSA-N

物化性质

• 沸点：
  908.8±65.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl 2-acetamido-2-deoxy-4-O-(alpha-L-fucopyranosyl)-3-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside 、 一水合肼 在 水 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以Lyophilization of the water gave 8-hydrazinocarbonyloctyl 2-acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-3-O-(β-D-galactopyranosyl)-β-D-glucopyranoside (14) in quantitative yield as an amorphous solid的产率得到8-hydrazinocarbonyloctyl 2-acetamido-2-deoxy-4-O-(alpha-L-fucopyranosyl)-3-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside
  参考文献：
  名称：

  Artificial oligosaccharide antigenic determinants

  摘要：

  含有糖苷键桥臂的碳水化合物抗原决定因子被合成并与载体分子耦合，形成人工抗原，并与固体支持物耦合，形成免疫吸附剂。制备了各种血型人工抗原，并展示了应用。具体示例包括制备Lewis-a、Lewis-b、A、B和H（O）血型抗原；制备针对这些人工抗原的抗血清；制备特异性抗体对这些抗原的免疫吸附剂，并检测这些抗原的存在。

  公开号：

  US04238473A1
• 作为产物：
  描述：

  methyl 8-{[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosamyl]oxy}nonanoate 、 5`-二磷酸鸟嘌呤核苷-岩藻糖二钠盐 在 3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase HEPES buffer 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 反应 0.5h， 生成 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-4-O-(alpha-L-fucopyranosyl)-3-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/0008-6215(96)00047-x

文献信息

• Glycoside-ether-ester compounds
  申请人：Chembiomed Limited

  公开号：US04137401A1

  公开（公告）日：1979-01-30

  Carbohydrate antigenic determinants containing a glycosidically linked bridging arm are synthesized and coupled to carrier molecules to form artificial antigens, and to solid supports to form immunoabsorbants. These artificial antigens are used to detect antibodies to the carbohydrate haptens, and to raise antisera specific for the carbohydrate antigenic determinants. The immunoabsorbants are used to purify or remove antibodies to the carbohydrate haptens. Specific examples are given to the synthesis of the Lewis-a, Lewis-b, B, and H(O) blood group antigens; to the preparation of antisera to these artificial antigens, and to the preparation of immunoabsorbants specific for antibodies to these antigens.

  含有糖苷桥臂的碳水化合物抗原决定因子被合成并耦合到载体分子上形成人造抗原，也耦合到固体支持物上形成免疫吸附剂。这些人造抗原用于检测抗碳水化合物半抗原的抗体，并提高特异性针对碳水化合物抗原决定因子的抗血清。免疫吸附剂用于纯化或去除抗碳水化合物半抗原的抗体。给出了具体示例，包括合成Lewis-a，Lewis-b，B和H（O）血型抗原，制备这些人造抗原的抗血清以及制备特异性针对这些抗原的免疫吸附剂。
• 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
• US4137401A
  申请人：——

  公开号：US4137401A

  公开（公告）日：1979-01-30
• US4238473A
  申请人：——

  公开号：US4238473A

  公开（公告）日：1980-12-09