1,2',3,3',4',6,6'-hepta-O-acetyl-N-acetyl-β-lactosamine | 51450-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2',3,3',4',6,6'-hepta-O-acetyl-N-acetyl-β-lactosamine
• 英文别名: 2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranose；2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside；2-acetoamido-1,3,6-tri-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranose；N-Acetyllactosamine heptaacetate 98%；[(2R,3S,4R,5R,6S)-5-acetamido-4,6-diacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 51450-25-0
• 化学式: C₂₈H₃₉NO₁₈
• 分子量: 677.614
• InChiKey: XKTWMUHXXMTTHP-JLZLBSMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  241
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1,2',3,3',4',6,6'-hepta-O-acetyl-N-acetyl-β-lactosamine 在 三氟甲磺酸三甲基硅酯 、 4-甲基苯磺酸吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 2-azidoethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  提供高特异性抗Gal免疫应答的α-Gal三糖表位的设计和合成†

  摘要：

  展示Galα（1,3）Gal表位的碳水化合物抗原可被人类天然存在的抗体识别。这些抗-Gal抗体最多占血清IgG的1％，并被认为是有害的，因为它们会导致超急性器官排斥。为了模拟这种情况，将α（1,3）半乳糖基转移酶敲除小鼠接种Galα（1,3）Gal表位。在我们的研究中，检查了由方酸酯部分连接的由Galα（1,3）Galβ（1,4）GlcNAc或Galα（1,3）Galβ（1,4）Glc组成的两个α-Gal三糖表位是否存在。它们在KO小鼠中引发免疫反应的能力。使用两组分酶促系统合成两个靶标表位，所述酶联体系使用含有用于偶联的接头部分的修饰的二糖底物。尽管两种糖缀合物疫苗均能诱导所需的高抗Gal IgG抗体滴度，但发现该反应对所用的Galα（1,3）Galβ（1,4）GlcNAc半抗原具有极高的特异性，而与Galα（ 1,3）Galβ（1,4）Glc半抗原。我们的发现表明，尽管同质的糖缀合物疫

  DOI：

  10.1039/c7ob00448f
• 作为产物：
  描述：

  1,2',3',4',6,6'-hexa-O-acetyl-3-O-benzyl-N-acetyl-β-lactosamine 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 1,2',3,3',4',6,6'-hepta-O-acetyl-N-acetyl-β-lactosamine
  参考文献：
  名称：

  Itoh, Yoshio; Tejima, Setsuzo, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 2, p. 727 - 729

  摘要：

  DOI：

文献信息

• Regioselective Deacetylation of Disaccharides via Immobilized<i>Aspergillus niger</i>Esterase(s)-catalyzed Hydrolysis in Aqueous and Non-aqueous Media
  作者：Teodora Bavaro、Pamela Torres-Salas、Nicola Antonioli、Carlo F. Morelli、Giovanna Speranza、Marco Terreni

  DOI：10.1002/cctc.201300388

  日期：2013.10

  adsorbed onto the employed matrices. These residual proteins were covalently immobilized on epoxy‐acrylic resin. Immobilized hydrolases were tested in the hydrolysis of acetylated disaccharides in water‐cosolvent systems. ANL‐Esterase was able to catalyze regioselective deprotection of acetylated β‐O‐methyl lactoside in C‐2 position and β‐O‐methyl lactosaminide in C‐3′ position. The hydrolyzed products

  从黑曲霉脂肪酶（ANL）的粗商业提取物中纯化的脂肪酶馏分被选择性地固定在疏水性支持物上。酯酶活性的显着百分比保留在上清液中，该酯酶活性源自无法吸附到所用基质上的酯酶。这些残留的蛋白质被共价固定在环氧丙烯酸树脂上。在水-助溶剂系统中测试了固定化水解酶在乙酰化二糖水解中的作用。ANL-酯酶能够催化C-2位和β- O上的乙酰化β- O-甲基乳糖苷的区域选择性脱保护-甲基乳糖苷位于C-3'位置。从未被报道过的水解产物可以被认为是合成具有生物学意义的寡糖的新基础。此外，还可以在叔丁醇中进行制备性水解。这种溶剂与ANL酯酶的稳定性兼容，并且由于其绿色状态而显得是一种新颖而有前途的方法。
• Glycosylation of dodecyl 2-acetamido-2-deoxy-β-d-glucopyranoside and dodecyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside as saccharide primers in cells
  作者：Toshinori Sato、Minako Takashiba、Rumi Hayashi、Xingyu Zhu、Tatsuya Yamagata

  DOI：10.1016/j.carres.2008.01.022

  日期：2008.4

  Syntheses of oligosaccharides expressed on cells are indispensable for the improvement of the functional analyses of the oligosaccharides and their applications. We are developing saccharide primers for synthesizing oligosaccharides using living cells. In this study, dodecyl 2-acetamido-2-deoxy-beta-D-glucopyranoside (GlcNAc-C12) and dodecyl beta-D-galactopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside (LacNAc-C12) were examined for their abilities to prime the syntheses of neolacto-series oligosaccharides in HL60 cells. When GlcNAc-C12 was incubated with HL60 cells in serum-free medium for 2 days, 14 kinds of glycosylated products were collected from the culture medium. They were separated by high-performance liquid chromatography. The sequences of the products were determined to be neolacto-series oligosaccharides including Lewis(X), sialyl Lewis(X), polylactosamine, and sialylpolylactosamine by mass spectrometry. GlcNAc-C12 was also glycosylated by B16 cells and gave sialyllactosamine. Furthermore, LacNAc-C12 gave similar glycosylated products to GlcNAc-C12. (C) 2008 Elsevier Ltd. All rights reserved.
• A chemoenzymatic approach towards moenomycin structural analogues
  作者：Gerhard Range、Ralf Krähmer、Peter Welzel、Dietrich Müller、Guido F. Herrmann、Udo Kragl、Christian Wandrey、Astrid Markus、Yveline van Heijenoort、Jean van Heijenoort

  DOI：10.1016/s0040-4020(96)01116-7

  日期：1997.2

  The trisaccharide moenomycin analogue 1c has been synthesized. One starting material was N-acetyllactosamine obtained by an enzyme-catalyzed transglycosylation. 1c differs from moenomycin degradation product 1a only in two positions of unit C. In contrast to 1a the synthetic 1c is antibiotically inactive. (C) 1997, Elsevier Science Ltd.