4-O-(4-O-alpha-吡喃半乳糖基-beta-吡喃半乳糖基)吡喃葡萄糖 | 80446-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-O-(4-O-alpha-吡喃半乳糖基-beta-吡喃半乳糖基)吡喃葡萄糖
• 中文别名: α-D-吡喃半乳糖基-(1-&gt4)-β-D-吡喃半乳糖基-(1-&gt4)-D-葡萄吡喃糖
• 英文名称: globotriose
• 英文别名: O-α-D-galactopyranosyl-(1-4)-O-β-D-galactopyranosyl-(1-4)-D-glucopyranose；alpha-D-Galp-(1->4)-beta-D-Galp-(1->4)-D-Glcp；(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 80446-87-3
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: FYGDTMLNYKFZSV-ANKSBSNASA-N

物化性质

• 沸点：
  865.2±65.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4-O-(4-O-alpha-吡喃半乳糖基-beta-吡喃半乳糖基)吡喃葡萄糖 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 生成 α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-D-glucitol
  参考文献：
  名称：

  碳水化合物测序的一致策略。1.通过MSn挖掘结构细节。

  摘要：

  该报告是三份系列报告中的第一份，主要针对建立一致的碳水化合物测序策略。这些报告分为（i）通过MSn分解解释小低聚物结构所有方面的分析考虑因素；（ii）使用离子片段库和相关工具进行高通量分析的数据库支持；以及（iii）用于分析的结论算法。从MSn拆卸途径定义寡糖拓扑结构。这份第一份报告的分析性贡献探索了通过离子阱质谱法暴露的结构细节的局限性，其中样品制备为甲基衍生物，并作为金属离子加合物进行了分析。这项数据挖掘工作着眼于将小寡聚物的片段与立体特异性聚糖结构相关联，结果归因于金属离子加合和分析物构象的结合。容易的糖苷裂解引入了一个不稳定性点（吡喃糖基-1-烯），该点在碰撞激活后会引发随后的环断裂。产物质量和离子强度随残基间键合，支化位置和单体立体化学而变化。过度碎片化是小型低聚物的特性，少数振荡器中的碰撞能量会通过大量碎片化消散。使用离子阱质谱仪将本报告中讨论的程序统一为单一策略，其灵敏度可预

  DOI：

  10.1021/ac050724z
• 作为产物：
  描述：

  1,2,3,6-tetra-O-benzoyl-4-O-<(2,3,6-tri-O-benzoyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-α-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到4-O-(4-O-alpha-吡喃半乳糖基-beta-吡喃半乳糖基)吡喃葡萄糖
  参考文献：
  名称：

  人Pk抗原决定簇的化学合成。

  摘要：

  1,2,3,6-四-O-苯甲酰基-4-O-（2,3,6-三-O-苯甲酰基-β-D-吡喃半乳糖基）-α-D-吡喃葡萄糖与2,3，在2,2,4,6-三甲基吡啶，三氟甲磺酸银和分子筛4 A存在下的1,2-二氯乙烷中的4,6-四-O-苄基-α-D-吡喃半乳糖基氯得到1,2,3,6 -四-O-苯甲酰基-4-O- [2,3,6-三-O-苯甲酰基-4-O-（2,3,4,6-四-O-苄基-α-D-吡喃半乳糖基） -β-D-吡喃半乳糖基]-α-D-吡喃葡萄糖。然后催化氢解和脱苯甲酰化得到4-O-（4-O-β-D-吡喃半乳糖基-β-D-吡喃半乳糖基）-D-吡喃葡萄糖，即人血型Pk-抗原决定簇。从1,2,3,6-四-O-苯甲酰基-4-O-（2,3,6-三-O-苯甲酰基-β-D-吡喃半乳糖基）-β-D进行相似的反应顺序-吡喃葡萄糖。

  DOI：

  10.1016/s0008-6215(00)90703-1

文献信息

• [EN] GLYCOPOLYMERS SEQUESTERING CARBOHYDRATE-BINDING PROTEINS<br/>[FR] GLYCOPOLYMÈRES SÉQUESTRANT DES PROTÉINES DE LIAISON AUX GLUCIDES
  申请人：POLYNEURON PHARMACEUTICALS AG

  公开号：WO2018167230A1

  公开（公告）日：2018-09-20

  The invention relates to polymers comprising carbohydrate ligands and moieties, respectively, that bind to carbohydrate-binding proteins (CBPs), as well as to these carbohydrate ligands, and to their use in diagnosis and therapy of diseases that are associated with CBP-mediated cytotoxicity, agglutinatination, or immune complex deposit formation. In particular, the invention relates to polymers comprising a multitude of said carbohydrate ligands and moieties, respectively, mimicking carbohydrates that are bound by CBPs which belong to the group of (i) bacterial exotoxins, (ii) agglutinins, and (iii) immune complex deposit-forming immunoglobulins. Furthermore, the invention relates to the use of these polymers and carbohydrate ligands and moieties respectively, in diagnosis as well as for the treatment of diseases that are associated with CBP-mediated cytotoxicity, agglutinatination, or immune complex deposit formation. In one embodiment, the polymer is polylysine.

  该发明涉及包含与结合碳水化合物结合蛋白（CBP）的碳水化合物配体和基团的聚合物，以及这些碳水化合物配体的使用，以及它们在与CBP介导的细胞毒性、凝集素作用或免疫复合物沉积形成相关的疾病的诊断和治疗中的应用。具体而言，该发明涉及包含大量所述碳水化合物配体和基团的聚合物，分别模拟被属于（i）细菌外毒素、（ii）凝集素和（iii）免疫复合物沉积形成免疫球蛋白所结合的碳水化合物。此外，该发明涉及在诊断以及治疗与CBP介导的细胞毒性、凝集素作用或免疫复合物沉积形成相关的疾病中使用这些聚合物和碳水化合物配体和基团。在一种实施方式中，聚合物是聚赖氨酸。
• Efficient synthesis of globoside and isogloboside tetrasaccharides by using β(1→3) N-acetylgalactosaminyltransferase/UDP-N-acetylglucosamine C4 epimerase fusion protein
  作者：Jun Shao、Jianbo Zhang、Przemyslaw Kowal、Yuquan Lu、Peng George Wang

  DOI：10.1039/b300831b

  日期：——

  The β(1→3) N-acetylgalactosaminyltransferase/UDP-N-acetylglucosamine C4 epimerase fusion protein was constructed and used in coupled enzymatic reactions to synthesize a variety of globotetraose and isoglobotetraose derivatives from the corresponding lactoside acceptors.

  构建了β(1→3)N-乙酰半乳糖胺基转移酶/UDP-N-乙酰葡萄糖胺C4差向异构酶融合蛋白，并将其用于耦合酶促反应，以相应的乳糖苷受体为原料合成了多种四糖和异四糖衍生物。
• Influence of Gb3 glycosphingolipids differing in their fatty acid chain on the phase behaviour of solid supported membranes: chemical syntheses and impact of Shiga toxin binding
  作者：Ole M. Schütte、Annika Ries、Alexander Orth、Lukas J. Patalag、Winfried Römer、Claudia Steinem、Daniel B. Werz

  DOI：10.1039/c4sc01290a

  日期：——

  The Shiga toxin B subunit (STxB), which is involved in cell membrane attachment and trafficking of Shiga holotoxin, binds specifically to the glycosphingolipid Gb3. In biological membranes, Gb3 glycosphingolipids differ in their fatty acid composition and there is strong evidence that the fatty acid alters the binding behaviour of STxB as well as the intracellular routing of the Shiga toxin/Gb3 complex. To analyse the binding of STxB to different Gb3s, we chemically synthesized saturated, unsaturated, α-hydroxylated Gb3s and a combination thereof, all based on a C24-fatty acid chain starting from monosaccharide building blocks, sphingosine and the respective fatty acids. These chemically well-defined Gb3s were inserted into solid supported phase-separated lipid bilayers composed of DOPC/sphingomyelin/cholesterol as a simple mimetic of the outer leaflet of animal cell membranes. By fluorescence- and atomic force microscopy the phase behaviour of the bilayer as well as the lateral organization of bound STxB were analysed. The fatty acid of Gb3 significantly alters the ratio between the ordered and disordered phase and induces a third intermediate phase in the presence of unsaturated Gb3. The lateral organization of STxB on the membranes varies significantly. While STxB attached to membranes with Gb3s with saturated fatty acids forms protein clusters, it is more homogeneously bound to membranes containing unsaturated Gb3s. Large interphase lipid redistribution is observed for α-hydroxylated Gb3 doped membranes. Our results clearly demonstrate that the fatty acid of Gb3 strongly influences the lateral organization of STxB on the membrane and impacts the overall membrane organization of phase-separated lipid membranes.

  志贺毒素B亚基（STxB）参与细胞膜附着和志贺毒素的转运，特异性地结合到糖神经酰胺Gb3上。在生物膜中，Gb3糖神经酰胺的脂肪酸组成不同，有强有力的证据表明脂肪酸改变STxB的结合行为以及志贺毒素/Gb3复合物的细胞内运输途径。为了分析STxB与不同Gb3的结合，我们化学合成了饱和、不饱和、α-羟基化的Gb3及其组合，所有这些都基于从单糖构建块、鞘氨醇和相应的脂肪酸开始的C24脂肪酸链。这些化学上定义明确的Gb3被插入到由DOPC/鞘磷脂/胆固醇组成的固相分离脂质双层中，作为动物细胞膜外叶的简单模拟物。通过荧光显微镜和原子力显微镜分析了双层的相行为以及STxB结合的侧向组织。Gb3的脂肪酸显著改变了有序和无序相的比例，并在存在不饱和Gb3的情况下诱导了第三种中间相。STxB在膜上的侧向组织显著变化。当STxB附着在含有饱和脂肪酸Gb3的膜上时形成蛋白质簇，它更均匀地结合到含有不饱和Gb3的膜上。观察到α-羟基化Gb3掺杂膜的大相间脂质重分布。我们的结果清楚地表明，Gb3的脂肪酸强烈影响STxB在膜上的侧向组织，并影响相分离脂质膜的整体膜组织。
• Recyclable benzyl-type fluorous tags: Preparation and application in oligosaccharide synthesis
  作者：Yong-Hai Chai、Ying-Le Feng、Jing-Jing Wu、Chu-Qiao Deng、Ai-Yun Liu、Qi Zhang

  DOI：10.1016/j.cclet.2017.06.020

  日期：2017.8

  Abstract We herein described the design, synthesis and application of two recyclable benzyl-type fluorous tags with double fluorous chains. The benzyl-type fluorous tags were prepared in 3 steps from a commercially available fluorous alcohol. The glycosylation of the benzyl-type tags with imidate donors proceeded smoothly to provide the corresponding fluorous-tagged carbohydrates in good to excellent

  摘要我们在此描述了两个具有双氟链的可循环利用的苄基型氟标签的设计，合成和应用。由市售的氟代醇分三步制备苄基型氟代标签。苄基型标签与亚氨酸酯供体的糖基化顺利进行，以良好至极佳的收率提供了相应的带氟标签的碳水化合物，这些糖很容易通过氟固相萃取（FSPE）纯化。在普通的催化加氢条件下，可以有效地从标签束缚的碳水化合物中除去标签，并且最初的苄基型氟标签可以通过两步简单的步骤以69％–93％的产率再生。通过FSPE辅助合成寡糖Gb3证明了新的苄基-氟标签的实用性。
• Total synthesis of globotriaosyl-E and Z-ceramides and isoglobotriaosyl-E-ceramide
  作者：Katsuya Koike、Mamoru Sugimoto、Susumu Sato、Yukishige Ito、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/0008-6215(87)80181-7

  日期：1987.6

  Stereoselective, total synthesis of O-alpha-D-galactopyranosyl-(1----4) -O-beta-D-galactopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----1)-N -tetracosanoyl-[2S,3R,4E (and 4Z)]-sphingenine and O-alpha-D -galactopyranosyl-(1----3)-O-beta-D-galactopyranosyl-(1----4)-O-beta-D -glucopyranosyl-(1----1)-N-tetracosanoyl-(2S,3R,4E)-sphin gen ine was achieved by using O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)

  O-α-D-吡喃半乳糖基-（1 ---- 4）-O-β-D-吡喃半乳糖基-（1 ---- 4）-O-β-D-吡喃葡萄糖基-（1-的立体选择性全合成--- 1）-N-十四烷酰基-[2S，3R，4E（和4Z）]-鞘氨醇和O-α-D-吡喃半乳糖基-（1 ---- 3）-O-β-D-吡喃半乳糖基-（通过使用O-（2,3）可实现1 ---- 4）-O-β-D-吡喃葡萄糖基-（1 ---- 1）-N-十四烷酰基-（2S，3R，4E）-斯宾碱，4,6-四-O-乙酰基-α-D-吡喃半乳糖基）-（1 ---- 4）-O-（2,3,6-三-O-乙酰基-β-D-吡喃半乳糖基）-（ 1 ---- 4）-2,3,6-三-O-乙酰基-α-D-吡喃葡萄糖基三氯乙酰亚氨酸酯，O-（2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基） -（1 ---- 4）-O-（2,3,6-三-O-乙酰基-β-D-吡喃半乳糖基）-（1