O-(β-D-glucopyranosyl)hydroxylamine | 390756-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(β-D-glucopyranosyl)hydroxylamine
• 英文别名: O-β-D-glucopyranosylhydroxylamine；1-O-amino-β-D-glucopyranoside；O-β-D-glucopyranosyl-oxyamine；aminooxy-β-d-glucopyranoside；β-D-glucopyranosyl-oxyamine；Glc-β-ONH2；(2S,3R,4S,5S,6R)-2-aminooxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 390756-31-7
• 化学式: C₆H₁₃NO₆
• 分子量: 195.172
• InChiKey: RHMWVNFRRRZAAQ-DVKNGEFBSA-N

物化性质

• 沸点：
  474.7±45.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O-(β-D-glucopyranosyl)hydroxylamine 在 盐酸 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 反应 40.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime
  参考文献：
  名称：

  Enantioselective catalysis. Part 142: Carbohydrate-derived oxime ethers from functionalised aldehydes and O-β-d-glucopyranosylhydroxylamine—new CN ligands stable towards hydrolysis

  摘要：

  A new way of linking carbohydrates to phosphorus- or nitrogen-containing aldehydes via oxime ethers is described resulting in novel C=N ligands which are stable towards hydrolysis. Reaction Of O-beta -D-glucopyranosythydroxylamine 2 with 2-diphenylphosphanylbenzaldehyde 3 or pyridine-2-carbaldehyde 4 afforded the oxime ethers O-(beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 5 and O-(beta -D-glucopyranosyl)pyridine-2-carbaldoxime 6. After peracetylation of the hydroxyl groups in 5 and 6, the protected sugar derivatives O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 7 and O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)pyridine-2-carbaldoxime 8 were obtained. The molecular structure of 7 was established by X-ray diffraction studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00451-7
• 作为产物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)pyrrolidine-2,5-dione 在 肼 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 O-(β-D-glucopyranosyl)hydroxylamine
  参考文献：
  名称：

  Multivalent presentation of carbohydrates by 3₁₄-helical peptide templates: synthesis, conformational analysis using CD spectroscopy and saccharide recognition

  摘要：

  一个四聚糖结合物模板，SSFT 1，与多种六个氨氧基糖偶联，以实现多价糖结合物2-7。

  DOI：

  10.1039/c5ob01673h

文献信息

• Inhibition of Mitosis by Glycopeptide Dendrimer Conjugates of Colchicine
  作者：David Lagnoux、Tamis Darbre、M. Lienhard Schmitz、Jean-Louis Reymond

  DOI：10.1002/chem.200401294

  日期：2005.6.20

  devices for colchicine. Colchicine was attached to the dendrimers at the cysteine thiol group through a disulfide or thioether linkage. The biological activities of the glycopeptide dendrimer conjugates were evaluated in HeLa tumor cells and non-transformed mouse embryonic fibroblasts (MEFs). The concentrations of glycopeptide dendrimer drug conjugates required to achieve inhibition of cell proliferation

  已经制备了糖肽树状聚合物，其表面上带有四个或八个相同的糖苷部分（β-葡萄糖，α-半乳糖，α-N-乙酰基半乳糖或乳糖），分支内的天然氨基酸（Ser，Thr，His，Asp ，Glu，Leu，Val，Phe），2,3-二氨基丙酸作为分支单元，并在核心保留一个半胱氨酸残基。这些树状聚合物已被用作秋水仙碱的药物递送装置。秋水仙碱通过二硫键或硫醚键连接到半胱氨酸硫醇基团的树枝状聚合物上。在HeLa肿瘤细胞和未转化的小鼠胚胎成纤维细胞（MEF）中评估了糖肽树状聚合物结合物的生物学活性。发现通过干扰微管蛋白系统达到抑制细胞增殖所需的糖肽树状聚合物结合物的浓度比秋水仙碱浓度要高（IC50> 1 microM）。另一方面，糖肽树状大分子缀合物抑制HeLa细胞的增殖比MEF的增殖有效20到100倍。相比之下，非糖基化树状大分子和秋水仙碱本身对HeLa细胞的选择性是10倍或更低。
• Genetically-encoded fragment-based discovery (GE-FBD) of glycopeptide ligands with differential selectivity for antibodies related to mycobacterial infections
  作者：Ying Chou、Elena N. Kitova、Maju Joe、Richard Brunton、Todd L. Lowary、John S. Klassen、Ratmir Derda

  DOI：10.1039/c7ob02783d

  日期：——

  Accurate identification of tuberculosis (TB), caused by Mycobacterium tuberculosis, is important for global disease management. Point-of-care serological tests may improve TB diagnosis; however, specificities of available serodiagnostics are sub-optimal. We employed genetically encoded fragment-based discovery (GE-FBD) to select ligands for antibodies directed against the mycobacterial cell wall component

  由结核分枝杆菌引起的结核病（TB）的准确识别对于全球疾病管理非常重要。现场护理血清学检查可以改善结核病的诊断；但是，可用血清学诊断的特异性欠佳。我们采用基因编码的基于片段的发现（GE-FBD）为针对分枝杆菌细胞壁成分lipoarabinomannan（LAM）（一种有效的抗原）的抗体选择配体。GE-FBD使用了10个8个七肽的噬菌体展示文库，并用LAM的阿拉伯呋喃糖基六糖片段进行了化学修饰（Ara 6）和抗LAM抗体CS-35作为诱饵。该选择产生了对CS-35具有增强的亲和力和选择性但对906.4321抗体不具有亲和力和选择性的糖肽，两者均以相当的亲和力结合Ara 6。掺入发现的配体Ara 6 -ANSSFAP，Ara 6 -DAHATLR和Ara 6 -TTYVVNP的多价测定法在CS-35和906.4321之间显示出高达19倍的区分度。单独使用Ara 6抗原无法区分这些抗体。因此，GE
• Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation
  作者：Shivaji A. Thadke、Mahesh Neralkar、Srinivas Hotha

  DOI：10.1016/j.carres.2016.04.022

  日期：2016.7

  including glucosyl, mannosyl, galactosyl, ribofuranosyl, arabinofuranosyl, lyxofuranosyl and xylofuranosyl using gold catalysis repertoire. The protocol is identified to be compatible for the synthesis of aminooxy glycosides of higher oligosaccharides as well.

  据报道，在金（III）催化的糖苷化条件下，用各种醛糖衍生的炔丙基1,2-原酸酯对羟基琥珀酰亚胺和羟基邻苯二甲酰亚胺进行了O-糖基化。使用金催化库，由相应的糖基原酸酯，包括葡萄糖基，甘露糖基，半乳糖基，核呋喃糖基，阿拉伯呋喃糖基，莱呋喃呋喃糖基和木呋喃糖基，合成了多种羟基琥珀酰亚胺基和羟基邻苯二甲酰亚胺基糖苷。该方案经鉴定也可用于高级寡糖的氨基氧基糖苷的合成。
• Access to Biomolecular Assemblies through One-Pot Triple Orthogonal Chemoselective Ligations
  作者：Mathieu Galibert、Olivier Renaudet、Pascal Dumy、Didier Boturyn

  DOI：10.1002/anie.201006867

  日期：2011.2.18

  Three into one will go: The consecutive combination of three orthogonal chemoselective reactions (oxime ligation, thioether addition, and copper(I)‐catalyzed alkyne–azide cycloaddition (CuAAC)) in a sequential one‐pot approach allows the syntheses of highly sophisticated biomolecular compounds without intervening isolations and protection schemes (see picture; ODN=oligodeoxynucleotide).

  三合一：将三个正交的化学选择性反应（肟连接，硫醚加成和铜（I）催化的炔-叠氮化物环加成（CuAAC））的连续组合按顺序一锅法进行即可合成高度复杂的生物分子无需介入分离和保护方案的化合物（参见图片； ODN =寡脱氧核苷酸）。
• A multi-ligation strategy for the synthesis of heterofunctionalized glycosylated scaffolds
  作者：Baptiste Thomas、Michele Fiore、Gour Chand Daskhan、Nicolas Spinelli、Olivier Renaudet

  DOI：10.1039/c4cc05451b

  日期：——

  Well-defined heterofunctionalized glycosylated scaffolds with unprecedented molecular combinations have been prepared using up to five different bioorthogonal ligations.

  使用高达五种不同的生物正交连接方法制备了具有前所未有的分子组合的明确定义的异功能化糖基支架。