O-α-L-fucopyranosyl oxyamine | 936356-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-L-fucopyranosyl oxyamine
• 英文别名: O-α-L-fucopyranosylhydroxylamine；α-O-L-fucopyranosyloxyamine；(2S,3S,4R,5S,6S)-2-aminooxy-6-methyloxane-3,4,5-triol
• CAS: 936356-58-0
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: GVYOGLYSDQUJBT-KGJVWPDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-α-L-fucopyranosyl oxyamine 、 Pent-4-enyl 2-methyl-3-(4-oxopentanoyloxy)-2-(4-oxopentanoyloxymethyl)propanoate 以 aq. buffer 为溶剂， 生成
  参考文献：
  名称：

  Bifunctional dendrons for multiple carbohydrate presentation via carbonyl chemistry

  摘要：

  合成了新的第0、1和2代的树状分子，焦点处带有双键，末端带有羰基。羰基被利用于通过还原胺化和烷氧胺共轭与样品糖类进行多价共轭。

  DOI：

  10.3762/bjoc.10.177
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-L-fucopyranose 在 二乙胺基三氟化硫 、 三氟化硼乙醚 、 三乙胺 、 甲基肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 13.5h， 生成 O-α-L-fucopyranosyl oxyamine
  参考文献：
  名称：

  α和βL-富勒基糖基氧胺：通过肟连接制备含岩藻糖的糖缀合物的关键中间体。

  摘要：

  我们在这里报道了通过肟连接制备糖簇的新的α和β氨基氧基化的L-富勒基糖基衍生物的合成。在三氟化硼-二乙基醚化物的存在下，进行了活化的三乙酰化L-呋喃核糖基氟与N-羟基邻苯二甲酰亚胺之间的糖基化反应，并比较了在二氯甲烷，乙腈或四氢呋喃中糖基化的立体化学结果。有趣的是，尽管在碳2处有一个乙酸酯参与基团，但仍获得了出乎意料的α和β端基异构体比率，特别是在乙腈中1，2-顺式糖基化反应非常有利。最终用甲基肼将所得的α和βN-氧基邻苯二甲酰亚胺基复核糖基衍生物脱保护，以获得相应的游离氨基氧基化的复核糖基。

  DOI：

  10.1016/j.carres.2007.02.003

文献信息

• Oxime-Based Synthesis of New Chromogenic and Fluorogenic Oligosaccharides
  作者：Olivier Renaudet、Pascal Dumy

  DOI：10.1002/ejoc.200800855

  日期：2008.11

  A new simple approach for the synthesis of labelled oligosaccharides is described. Free synthetic carbohydrate recognition building blocks were conjugated with fluorogenic and chromogenic dyes under mild experimental conditions by using oxime ligation. The resulting oligosaccharide probes presenting well-defined anomer configuration might find broad interests for recognition studies with a large panel

  描述了一种新的简单的标记寡糖合成方法。在温和的实验条件下，通过使用肟连接，将游离的合成碳水化合物识别构建块与荧光和显色染料缀合。由此产生的寡糖探针呈现出明确定义的异头构型，可能会引起对大量碳水化合物结合蛋白的识别研究的广泛兴趣。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Phage-displayed macrocyclic glycopeptide libraries
  作者：Simon Ng、Ratmir Derda

  DOI：10.1039/c5ob02646f

  日期：——

  In this report, we describe an efficient way to generate libraries of macrocyclic glycopeptides in one step by reacting phage-displayed libraries of peptides with dichloro-oxime derivatives. We showed that the reactions do not interfere with the ability of phage to replicate in bacteria. The reactions are site-selective for phage-displayed peptides and they do not modify any other proteins of phage

  在这份报告中，我们描述了一种通过一步将噬菌体展示的肽库与二氯肟衍生物反应来生成大环糖肽库的有效方法。我们表明该反应不会干扰噬菌体在细菌中复制的能力。该反应对于噬菌体展示的肽是位点选择性的，并且它们不修饰噬菌体的任何其他蛋白质。本报告中描述的技术将有助于遗传选择各种聚糖结合蛋白的大环糖肽。
• Multivalent Glycomimetics with Affinity and Selectivity toward Fucose-Binding Receptors from Emerging Pathogens
  作者：David Goyard、Veronica Baldoneschi、Annabelle Varrot、Michele Fiore、Anne Imberty、Barbara Richichi、Olivier Renaudet、Cristina Nativi

  DOI：10.1021/acs.bioconjchem.7b00616

  日期：2018.1.17

  Bacterial and fungal pathogens involved in lung infection in cystic fibrosis patients utilize a particular family of glycan-binding proteins, characterized by the presentation of six fucose-binding sites on a ring-shaped scaffold. These lectins are attractive targets for anti-infectious compounds that could interfere in the recognition of host tissues by pathogens. The design of a cyclopeptide-based hexavalent structure allowed for the presentation of six fucose residues. The synthetic hexavalent compound displays liable geometry resulting in high-avidity binding by lectins from Aspergillus fumigatus and Burkholderia ambifaria. Replacing the fucose residue with a conformationally constrained fucomimetic does not alter the affinity and provides fine specificity with no binding to other fucose-specific lectins.

  导致囊性纤维化患者肺部感染的细菌和真菌病原体利用一种特殊的糖结合蛋白家族，其特点是在环形支架上呈现六个岩藻糖结合位点。这些凝集素是抗感染化合物的诱人靶点，可以干扰病原体对宿主组织的识别。设计一种基于环肽的六价结构可以呈现六个岩藻糖残基。这种合成的六价化合物显示出合理的几何形状，因此能与曲霉菌和埋伏伯克霍尔德氏菌的凝集素产生高活性结合。用构象受限的岩藻糖模拟物取代岩藻糖残基不会改变亲和力，而且具有很好的特异性，不会与其他岩藻糖特异性凝集素结合。
• High Affinity Glycodendrimers for the Lectin LecB from Pseudomonas aeruginosa
  作者：Nathalie Berthet、Baptiste Thomas、Isabelle Bossu、Emilie Dufour、Emilie Gillon、Julian Garcia、Nicolas Spinelli、Anne Imberty、Pascal Dumy、Olivier Renaudet

  DOI：10.1021/bc400239m

  日期：2013.9.18

  Following an iterative oxime ligation procedure, cyclopeptide (R) and lysine-based dendron (D) were combined in all possible arrangements and successively functionalized with alpha-fucose and beta-fucose to provide a new series of hexadecavalent glycosylated scaffolds (i.e., scaffolds RD16, RR16, DR16 and DD16). These compounds and smaller analogs (tetra- and hexavalent scaffolds R-4 and R-6) were used to evaluate the influence of the ligand valency and architecture, and of the anomer configuration in the binding to the alpha Fuc-specific lectin LecB from Pseudomonas aeruginosa. Competitive enzyme-linked lectin assays (ELLA) revealed that only the RD16 architecture displaying alpha Fuc (9A) reaches strong binding improvement (IC50 of 0.6 nM) over alpha MeFuc, and increases the alpha-selectivity of LecB. Dissociation constant of 28 nM was measured by isothermal titration micorcalorimetry (ITC) for 9A, which represents the highest affinity ligand ever reported for LecB. ITC and molecular modeling suggested that the high affinity observed might be due to an aggregative chelate binding involving four sugar head groups and two lectins. Interestingly, unprecedented binding effects were observed with beta-fucosylated conjugates, albeit being less active than the corresponding ligands of the alpha Fuc series. In particular, the more flexible lysine-based dendritic structures (15B and 18B) showed a slight inhibitory enhancement in comparison with those having cyclopeptide core.