allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside | 149429-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: allyl 2-acetamido-3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside；Gal2Ac3Ac4Ac6Ac(b1-4)GlcNAc3Ac6Ac(b)-O-allyl；[(2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-6-prop-2-enoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 149429-76-5
• 化学式: C₂₉H₄₁NO₁₇
• 分子量: 675.641
• InChiKey: CIKUQWROYLYXTE-JVUXCJQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  224
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranoside 在 二甲基硫 、 sodium methylate 、 sodium cyanoborohydride 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 22.5h， 生成 2-[(2-pyridyl)amino]ethyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 2-[(2-pyridyl)amino]ethyl β-d-lactosaminide and evaluation of its acceptor ability for sialyltransferase: a comparison with 4-methylumbelliferyl and dansyl β-d-lactosaminide

  摘要：

  We report the synthesis Of P-D-lactosaminide with a 2-aminopyridyl group that is linked to a glycosyl tether at the reducing end. This fluorescent disaccharide acts as an acceptor for both alpha-(2 --> 6)- and alpha-(2 --> 3)-sialyltransferases. In addition, the acceptor ability of this disaccharide was evaluated and compared with that Of beta-D-lactosaminide having a dansyl or a 4-methylumbelliferyl group. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.015
• 作为产物：
  描述：

  在 吡啶 、 乙二胺 作用下， 以 甲醇 、 乙醇 、 正丁醇 为溶剂， 反应 44.0h， 生成 allyl 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：

  The development of new molecular tools containing a chemically synthesized carbohydrate ligand for the elucidation of carbohydrate roles via photoaffinity labeling: Carbohydrate–protein interactions are affected by the structures of the glycosidic bonds and the reducing-end sugar

  摘要：

  Photoaffinity labeling technology is a highly efficient method for cloning carbohydrate-binding proteins. When the carbohydrate probes are synthesized according to conventional methods, however, the reducing terminus of the sugar is opened to provide an acyclic structure. Our continued efforts to solve this problem led to the development of new molecular tools with an oligosaccharide structure that contains a phenyldiazirine group for the elucidation of carbohydrate-protein interactions. We investigated whether carbohydrate-lectin interactions are affected by differences in the glycosidic formation and synthesized three types of molecular tools containing Galp-GlcpNAc disaccharide ligands and a photoreactive group (1, 2, 3). Photoaffinity labeling validated the recognition of the new ligand by different glycosidic bonds. Photoaffinity labeling also demonstrated that both the reducing end sugar and non-reducing end sugar recognized the Erythrina cristagalli agglutinin.

  DOI：

  10.1016/j.bmc.2014.06.049

文献信息

• Synthesis of Benzaldehyde-Functionalized Glycans: A Novel Approach Towards Glyco-SAMs as a Tool for Surface Plasmon Resonance Studies
  作者：Sebastian Kopitzki、Knud J. Jensen、Joachim Thiem

  DOI：10.1002/chem.200902693

  日期：——

  In recent years the interest in tools for investigating carbohydrate–protein (CPI) and carbohydrate‐carbohydrate interactions (CCI) has increased significantly. For the investigation of CPI and CCI, several techniques employing different linking methods are available. Surface plasmon resonance (SPR) imaging is a most appropriate tool for analyzing the formation of self‐assembled monolayers (SAM) of

  近年来，人们对研究碳水化合物-蛋白质（CPI）和碳水化合物-碳水化合物相互作用（CCI）的工具的兴趣大大增加。为了调查CPI和CCI，可以使用几种采用不同链接方法的技术。表面等离振子共振（SPR）成像是分析碳水化合物衍生物可模仿糖萼的自组装单分子膜（SAM）形成的最合适工具。与先前用于分析CPI和CCI的SPR成像方法相反，本文报道的新颖方法可轻松，快速地合成接头间隔子和碳水化合物衍生物，并通过控制配体的数量和方向来增强结合作用。为了通过还原胺化固定在具有生物排斥性的氨基官能化SPR芯片上，已通过包括烯烃复分解在内的几个简便步骤合成了多种醛官能化的聚糖结构（葡萄糖，半乳糖，甘露糖，葡糖胺，纤维二糖，乳糖和乳糖胺）。提出了针对凝集素伴刀豆球蛋白A的有效固定方法和首次结合研究。
• Fluorescently Labeled Substrates for Monitoring α1,3‐Fucosyltransferase IX Activity
  作者：Nathalie Lunau、Katrin Seelhorst、Stefanie Kahl、Kathrin Tscherch、Christina Stacke、Sascha Rohn、Joachim Thiem、Ulrich Hahn、Chris Meier

  DOI：10.1002/chem.201302601

  日期：2013.12.16

  metastasis. Fucosyltransferases catalyze the transfer of fucose residues from the activated donor molecule GDP‐β‐L‐fucose to various acceptor molecules. However, detailed information about the reaction processes is still lacking for most fucosyltransferases. In this work we have monitored α1,3‐fucosyltransferase activity. For both donor and acceptor substrates, the introduction of a fluorescent ATTO dye

  岩藻糖基化通常是聚糖生物合成的最后一个过程。由此产生的聚糖参与多种生物过程，如细胞粘附、炎症或肿瘤转移。岩藻糖基转移酶催化从活化的供体分子 GDP-β- L转移岩藻糖残基-岩藻糖到各种受体分子。然而，大多数岩藻糖基转移酶仍然缺乏有关反应过程的详细信息。在这项工作中，我们监测了 α1,3-岩藻糖基转移酶的活性。对于供体和受体底物，荧光 ATTO 染料的引入是合成的最后一步。随后通过 α1,3-岩藻糖基转移酶将这些底物转化为荧光标记的产物，通过高效薄层色谱结合质谱以及双色荧光互相关光谱进行检查，结果表明两种荧光标记的供体 GDP -β - L-岩藻糖-ATTO 550 和受体N-乙酰乳糖胺-ATTO 647N 被重组人岩藻糖基转移酶 IX 接受，分别为幽门螺杆菌α1,3-岩藻糖基转移酶。荧光互相关光谱分析允许对酶促反应的进程进行快速和通用的估计，因此该方法可用作研究岩藻糖基转移酶反应的替代方法。
• Novel Synthetic Approaches to Manβ1-4GLCNAc and Lex Units from N-Acetyllactosamine
  作者：Ken-ichi Sato、Hiroshi Seki、Akira Yoshitomo、Hiroshi Nanaumi、Yoshimitsu Takai、Yoshiharu Ishido

  DOI：10.1080/07328309808002347

  日期：1998.5.1

  Regioselective protection of N-acetyllactosamine with triphenylmethyl (trityl) and pivaloyl groups afforded the corresponding 3, 2', 4'-tri- and 2',4'-dihydroxyl derivatives in a few steps, respectively; these derivatives were used efficiently for the syntheses of the title compounds from N-acetyllactosamine in 46% (7 steps) and 19% (8 steps) overall yields, respectively.