2-(((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid | 476213-99-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid
• 英文别名: carboxymethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside；2-[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyacetic acid
• CAS: 476213-99-7
• 化学式: C₁₆H₂₂O₁₂
• 分子量: 406.343
• InChiKey: TWWYGXIQWBPJMT-VMMWWAARSA-N

物化性质

• 沸点：
  518.6±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成
  参考文献：
  名称：

  Multivalent Nanofibers of a Controlled Length: Regulation of Bacterial Cell Agglutination

  摘要：

  Control of the size and shape of molecular assemblies on the nanometer scale in aqueous solutions is very important for the regulation of biological functions. Among the well-defined supramolecular structures of organic amphiphiles, one-dimensional nanofibers have attracted much attention because of their potential applications in biocompatible materials. Although much progress has been made in the field of self-assembled nanofobers, the ability to control the fiber length remains limited. The approach for control of the fiber length presented herein overcomes this limitation through the coassembly of amphiphilic rod-coil molecules in which the crystallinity of the aromatic segment can be regulated by pi-pi stacking interactions. The introduction of carbohydrate segments into the fiber exterior endows the nanofibers with the ability to adhere to bacterial cells. Notably, the fiber length systematically regulates the agglutination and proliferation of bacterial cells exposed to these fibers.

  DOI：

  10.1021/ja306802m
• 作为产物：
  描述：

  (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(benzyloxy)-2-oxoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 以70%的产率得到2-(((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid
  参考文献：
  名称：

  3-Trifluoromethyl-3-aryldiazirine photolabels with enhanced ambient light stability

  摘要：

  设计、合成和评价了环境光稳定的3-三氟甲基-3-芳基重氮烯光标。除了增强环境光稳定性外，改良后的光标在标记生物靶标方面同样高效。新的光标还将光亲和标记物的水溶性提高了数倍。

  DOI：

  10.1039/c5cc09518b

文献信息

• Orthogonally Protected Cyclo-β-tetrapeptides as Solid-Supported Scaffolds for the Synthesis of Glycoclusters
  作者：Pasi Virta、Marika Karskela、Harri Lönnberg

  DOI：10.1021/jo052348o

  日期：2006.3.1

  4-methyltrityl (Mtt) and 1-methyl-1-phenylethyl protections (PhiPr) exposes the β-amino and carboxyl terminus, respectively, and on-resin cyclization then gives the desired orthogonally protected cyclo-β-tetrapeptides (1 and 2). The α-amino groups, bearing the Fmoc and Alloc protections and the azide mask, allow stepwise orthogonal derivatization of these solid-supported cyclo-β-tetrapeptide cores (1 and 2). This

  两个新型肽支架，即。环[（Ñ α -alloc）DPR-β-ALA-（Ñ α -Fmoc）DPR-β丙氨酸]（1）和环[（Ñ α -alloc）DPR-α叠氮基β-aminopropanoyl-（Ñ已经描述了由正交保护的2，3-二氨基丙酰基（Dpr）和β-丙氨酰基残基组成的α -Fmoc）Dpr-β-ALA]（2）。主链酰胺接头衍生树脂上的Fmoc化学已用于链组装。选择性去除4-甲基三苯甲基（Mtt）和1-甲基-1-苯乙基保护基（PhiPr）分别暴露β-氨基和羧基末端，然后在树脂上环化，得到所需的正交保护的环β-四肽（1和2）。带有Fmoc和Alloc保护以及叠氮掩膜的α-氨基可逐步逐步衍生这些固体负载的环β-四肽核（1和2）。这已经通过各种糖单元[即附着物证明的，乙酰基或甲苯甲酰基保护的羧甲基α-。d -glycopyranosides（13 - 15）和甲基6- ø - （4-硝基苯氧基羰基）-α-
• A Synthetic MUC1 Anticancer Vaccine Containing Mannose Ligands for Targeting Macrophages and Dendritic Cells
  作者：Markus Glaffig、Natascha Stergiou、Sebastian Hartmann、Edgar Schmitt、Horst Kunz

  DOI：10.1002/cmdc.201700646

  日期：2018.1.8

  A MUC1 anticancer vaccine equipped with covalently linked divalent mannose ligands was found to improve the antigen uptake and presentation by targeting mannose‐receptor‐positive macrophages and dendritic cells. It induced much stronger specific IgG immune responses in mice than the non‐mannosylated reference vaccine. Mannose coupling also led to increased numbers of macrophages, dendritic cells, and

  发现具有共价连接的二价甘露糖配体的MUC1抗癌疫苗可通过靶向甘露糖受体阳性的巨噬细胞和树突状细胞来改善抗原的摄取和呈递。与非甘露糖基化参考疫苗相比，它在小鼠中诱导出更强的特异性IgG免疫反应。甘露糖偶联还导致局部淋巴器官中巨噬细胞，树突状细胞和CD4 + T细胞数量增加。二价和四价甘露糖配体的比较显示四价形式的结合增加，表明更高的化合价可改善与甘露糖受体的结合。甘露糖偶联疫苗和非甘露糖基化参考疫苗诱导的IgG抗体对人乳腺肿瘤细胞的结合相似。
• Photoactivatable probes and uses thereof
  申请人：Manetsch Roman

  公开号：US10067136B1

  公开（公告）日：2018-09-04

  Provided herein are pyridyl- and pyrimidyl-containing diazirines that can be photoactivateable probes and formulations thereof. Also provided herein are photoaffinity labels that can include the pyridyl- and pyrimidyl-containing diazirines provided herein. Also provided herein are methods of using the photoactivatable probes and photoaffinity labels provided herein in a photoaffinity labeling reaction and/or assay.

  本文提供了含吡啶基和嘧啶基的重氮烯，可用作光活化探针及其配方。本文还提供了可以包含本文提供的吡啶基和嘧啶基的光亲和标记物。本文还提供了使用本文提供的光活化探针和光亲和标记物进行光亲和标记反应和/或测定的方法。
• Synthesis of new mono- and disaccharidic carboxymethylglycoside lactones (CMGLs) and their use toward 1,2-bisfunctionalized carbohydrate synthons
  作者：Rouba Cheaib、Arkadiusz Listkowski、Stéphane Chambert、Alain Doutheau、Yves Queneau

  DOI：10.1016/j.tetasy.2008.07.016

  日期：2008.8

  A general and convenient access to mono- and disaccharidic carboxymethyl glycoside lactones (CMGLs) is described. By taking advantage of the free OH at the 2-position, obtained after the opening of CMGLs by amines, the synthesis of a series of new 1,2-bisfunctionalized carbohydrate synthons is reported.

  描述了单和二糖基羧甲基糖苷内酯（CMGLs）的一般和方便访问。通过利用由胺打开CMGL之后在2-位获得的游离OH，报道了一系列新的1,2-双官能化碳水化合物合成子的合成。
• Synthesis of regioisomeric maltose-based Man/Glc glycoclusters to control glycoligand presentation in 3D space
  作者：Sven Ole Jaeschke、Ingo vom Sondern、Thisbe K. Lindhorst

  DOI：10.1039/d1ob01150b

  日期：——

  The investigation of carbohydrate recognition in a natural environment suffers from the complexity of overlapping functional effects such as multivalency and heteromultivalency effects. Another key factor in carbohydrate recognition is the presentation mode of glycoligands in three-dimensional (3D) space. In order to trace out the effect of 3D ligand presentation, we utilized an oligosaccharide model

  自然环境中碳水化合物识别的研究受到重叠功能效应的复杂性的影响，例如多价和异多价效应。碳水化合物识别的另一个关键因素是糖配体在三维 (3D) 空间中的呈现方式。为了追踪 3D 配体呈现的影响，我们利用寡糖模型来精确控制甘露糖配体 (Man) 和葡萄糖部分 (Glc) 之间的空间关系。二糖（麦芽糖）作为支架在合成麦芽糖苷的 6 和 6' 位交替缀合 Man 和 Glc，产生一对区域异构异二价糖簇。这种特定结构调整的生物学效应在采用活的甘露糖特异性粘附的天然系统中进行了测试。大肠杆菌细胞。事实上，Man 配体的可变 3D 呈现导致作为细菌粘附抑制剂的区域异构异二价糖簇之间存在 2 倍的差异。这可以被认为是一种显着的效果，这可以通过细菌凝集素和合成区域异构糖配体之间的复合物的计算机辅助建模来解释。