O-(β-D-galactopyranosyl)hydroxylamine | 170590-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(β-D-galactopyranosyl)hydroxylamine
• 英文别名: O-β-D-galactopyranosyl hydroxylamine；O-β-D-galactopyranosylhydroxylamine；β-D-1-O-hydroxylamino-galactose；1-O-amino-β-D-galactopyranoside；Gal-β-ONH2；(2S,3R,4S,5R,6R)-2-aminooxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 170590-90-6
• 化学式: C₆H₁₃NO₆
• 分子量: 195.172
• InChiKey: RHMWVNFRRRZAAQ-PHYPRBDBSA-N

物化性质

• 熔点：
  156 °C
• 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-galactopyranosyl)hydroxylamine 在 吡啶 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-diphenylphosphanylbenzaldoxime
  参考文献：
  名称：

  Enantioselective catalysis. Part 148: Carbohydrate-derived oxime ethers stable towards hydrolysis—syntheses of ligands and complexes and a study of their catalytic properties

  摘要：

  The synthesis of new hydrolytically stable oxime ether ligands by condensation of various aldehydes with O-beta-D-glucopyranosylhydroxylamine 1 or O-beta-D-galactopyranosylhydroxylamine 4 is described. After peracetylation of the hydroxyl groups, ligands soluble in organic solvents were obtained. The ligands have been tested in transition metal-catalysed reactions. Phosphorus-containing ligands gave high yields in palladium-catalysed allylic alkylation and rhodium-catalysed hydrosilylation reactions although the enantioselectivities were low. A 1,3-diphenylallyl-palladium(II) complex of ligand 2b was prepared and its structure was established by X-ray diffraction analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00093-4
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 tetrabutyl hydrogensulfate 、 氢溴酸 、 sodium carbonate 、 溶剂黄146 、 肼 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 O-(β-D-galactopyranosyl)hydroxylamine
  参考文献：
  名称：

  In Situ Preparation of β-d-1-O-Hydroxylamino Carbohydrate Polymers Mediated by Galactose Oxidase

  摘要：

  [GRAPHICS]Galactose oxidase produced a C-6 aldehyde in various terminal-containing galactose hydroxylamines for the simultaneous in situ generation of an A-B type condensation for the construction of unique oxime polymers. Molecular weights of the corresponding polymers were determined to be in the range of 4200-8900 g/mol, respectively. This indicates that approximately 20-25 sugar units were incorporated in these unique polymers.

  DOI：

  10.1021/ol0258379

文献信息

• Multivalent presentation of carbohydrates by 3₁₄-helical peptide templates: synthesis, conformational analysis using CD spectroscopy and saccharide recognition
  作者：Nitin J. Pawar、Ulf Diederichsen、Dilip. D. Dhavale

  DOI：10.1039/c5ob01673h

  日期：——

  A tetrameric glycoconjugate template, SSFT 1, was coupled with a variety of six aminooxy sugars to achieve multivalent glycoconjugates 2–7.

  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。
• Stereoselective phase transfer catalyzed syntheses of glycosyloxysuccinimides and their transformations into glycoprobes
  作者：Suoding Cao、François D. Tropper、René Roy

  DOI：10.1016/0040-4020(95)00325-3

  日期：1995.6

  Glycosyloxysuccinimides of D-galactose, D-glucose, N-acetyl-D-glucosamine, lactose, maltose (7–11) and sialic acid (13) were prepared from their glycosyl halides under PTC conditions. Ring opening of the succinimide moieties occurred with sodium hydroxide or methoxide to provide extended aglycons, while treatment of 8 with hydrazine afforded O-galactopyranosylhydroxylamine 17. Treatment of 9 with

  D-半乳糖，D-葡萄糖，N-乙酰基-D-葡萄糖胺，乳糖，麦芽糖（7-11）和唾液酸（13）的糖基氧基琥珀酰亚胺是在PTC条件下由它们的糖基卤化物制备的。琥珀酰亚胺部分的开环发生与氢氧化钠或甲醇盐，以提供延长的糖苷配基，而用肼处理8提供O- galactopyranosylhydroxylamine 17。用三（2-氨基乙基）胺处理9得到二价簇20，其在用异硫氰酸荧光素进一步处理后提供二价糖探针21。
• Fragment-based development of triazole-substituted O-galactosyl aldoximes with fragment-induced affinity and selectivity for galectin-3
  作者：Johan Tejler、Bader Salameh、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1039/b909091f

  日期：——

  A fragment-based development of 3C-triazol-1-yl-O-galactopyranosyl aldoximes led to the discovery of highly selective and high affinity (Kd down to 11 μM) small monosaccharide based inhibitors of galectin-3. Galectin-7, 8 N-terminal CRD, and 9 N-terminal CRD bound the inhibitors only weakly. The galectin-3 selectivity was hypothesized to stem from interaction of the aldoxime moiety with a site not

  基于片段的3C-三唑-1-基-O-半乳糖吡喃糖基醛肟的开发导致发现了基于半乳糖的高选择性和高亲和力（K d降至11μM）的小半乳糖半乳糖凝集素3抑制剂。Galectin-7、8个N末端CRD和9个N末端CRD仅弱结合了抑制剂。假设galectin-3的选择性源自醛肟部分与其他galectin中不存在的位点之间的相互作用。
• 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。
• Synthetic peptides, conjugation reagents and methods
  申请人：——

  公开号：US20030073157A1

  公开（公告）日：2003-04-17

  The invention provides methods and compositions useful for making synthetic peptide conjugates. In one embodiment, the invention provides compositions comprising the structure: 1 wherein R is selected from lower substituted or unsubstituted alkyl, O, NH and S and P is an amine protection group. In more particular embodiments, the compositions comprise &agr;-amine protected 4,5-dehydroleucine or &agr;-amine protected (2S)-aminolevulinic acid and/or P is F-moc. These compounds may be incorporated into peptides, for example, peptides comprising a substituted or unsubstituted (2S)-aminolevulinic acid residue, such as (2S)-aminolevulinic acid residue is substituted with an O- or N-linked glycoconjugate, or a detectable label.

  本发明提供了用于制备合成肽共轭物的方法和组合物。在一种实施例中，本发明提供了包括结构的组合物：1，其中R选自较低的取代或未取代烷基，O，NH和S，P是氨保护基。在更具体的实施例中，组合物包括α-氨基保护的4,5-去氢亮氨酸或α-氨基保护的（2S）-5-氨基戊酸和/或P是F-moc。这些化合物可以被纳入到肽中，例如，肽包括取代或未取代的（2S）-5-氨基戊酸残基，例如（2S）-5-氨基戊酸残基被O-或N-连接的糖结合物或可检测标记所取代。