4-nitrophenyl (α-D-galactopyranosyl)-(1->3)-α-D-galactopyranoside | 110891-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl (α-D-galactopyranosyl)-(1->3)-α-D-galactopyranoside
• 英文别名: 4-nitrophenyl α-D-galactopyranosyl-(1->3)-α-D-galactopyranoside；4-nitrophenyl α-D-galactopyranosyl-[1->3]-α-D-galactopyranoside；p-nitrophenyl-α-D-galactopyranosyl-(1->3)-α-D-galactopyranoside；α-D-Galp-(1->3)-α-D-Galp-O-p-NO2Ph；p-Nitrophenyl 3-O-alpha-D-galactopyranosyl-alpha-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 110891-71-9
• 化学式: C₁₈H₂₅NO₁₃
• 分子量: 463.395
• InChiKey: LBTDRWMZFQVCAR-QMBVPDPMSA-N

物化性质

• 沸点：
  814.5±65.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  224
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl (α-D-galactopyranosyl)-(1->3)-α-D-galactopyranoside 在 copper(II) sulfate 、 锌 作用下， 反应 1.0h， 生成 p-aminophenyl 3-O-(α-D-galactopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of Galα1-3Gal, Galα1-3Galβ1-4GlcNAc and their PEG-conjugates.

  摘要：

  Gal alpha 1-3Gal-pNP was prepared enzymatically from Gal-pNP using alpha-galactosidase from coffee beans. PEG was attached after the reduction of nitro group into amino group to give Gal alpha 1-3Gal-PEG conjugate. After removing the pNP group in Gal alpha 1-3Gal-pNP, the obtained disaccharide was used for the synthesis of Gal alpha 1-3Gal beta 1-4GlcNAc and corresponding trisaccharide-PEG conjugate. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00017-6
• 作为产物：
  描述：

  4-硝基苯基-α-D-吡喃半乳糖苷 在 α-D-galactosidase from Trichoderma reesei 作用下， 以 水 为溶剂， 以60%的产率得到4-nitrophenyl α-D-galactopyranosyl-(1->6)-α-D-galactopyranoside
  参考文献：
  名称：

  Transglycosylation activity of α-d-galactosidase from Trichoderma reesei An investigation of the active site

  摘要：

  The transglycosylation reaction catalyzed by alpha-D-galactosidase from the mycelial fungus Trichoderma reesei was studied using p-nitrophenyl alpha-D-galactopyranoside (PNPG). An aliphatic alcohol or the substrate itself can be an acceptor of the galactose residue in this reaction. The transglycosylation products were identified as alkyl galactosides in the case of alcohols or as galactobioside and galactotrioside in the case of PNPG. The transglycosylation rates follow a first-order equation with respect to the alcohol concentrations except for methanol. Affinities of some substrates were estimated from their K-i values in the reaction of the enzyme with PNPG. Transglycosylation of the substrate suggests a model for the enzyme active center. It is proposed that the active center includes two galactose-binding sites and a hydrophobic site. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00229-2
• 作为试剂：
  描述：

  alpha-D-半乳糖 、 p-aminophenyl 3-O-β-D-galactopyranosyl-α-D-galactopyranoside 、 β-Gal-(1->3)-α-Gal-OC6H4NO2-p 在 钯 4-nitrophenyl (α-D-galactopyranosyl)-(1->3)-α-D-galactopyranoside 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以to give (50 mg) as a yellowish solid的产率得到4-nitrophenyl (α-D-galactopyranosyl)-(1->3)-α-D-galactopyranoside
  参考文献：
  名称：

  Conjugates comprising galactose &agr;1,3 galactosyl epitopes and methods of using same

  摘要：

  该发明提供了用于异种移植的共轭物，其包括与价态平台分子共轭的半乳糖α1,3半乳糖基（αGal）表位，优选为化学定义的价态平台分子，该分子允许精确的价态。该发明还提供了包含这些共轭物的组合物，以及使用这些共轭物和组合物的方法（例如诱导耐受的方法）。

  公开号：

  US06399578B1

文献信息

• α-Galactobiosyl units: thermodynamics and kinetics of their formation by transglycosylations catalysed by the GH36 α-galactosidase from Thermotoga maritima
  作者：Anna S. Borisova、Dina R. Ivanen、Kirill S. Bobrov、Elena V. Eneyskaya、Georgy N. Rychkov、Mats Sandgren、Anna A. Kulminskaya、Michael L. Sinnott、Konstantin A. Shabalin

  DOI：10.1016/j.carres.2014.11.003

  日期：2015.1

  a limiting factor for application of the enzyme in the directed synthesis of oligogalactosides. However, this property can be used as a convenient tool in studies of thermodynamics of a glycosidic bond. Here, a novel approach to energy difference estimation is suggested. Both transglycosylation and hydrolysis of three types of galactosidic linkages were investigated using total kinetics of formation

  来自滨海嗜热菌（TmGal36A）的α-半乳糖苷酶的广泛区域选择性是该酶在寡半乳糖苷的定向合成中应用的限制因素。但是，该性质可以用作研究糖苷键热力学的方便工具。在此，提出了一种新的能量差估计方法。使用由海藻T.36（一种保留性的外泌作用糖苷水解酶）的单体糖苷水解酶家族36α-半乳糖苷酶催化的pNP-半乳糖苷的形成和水解的总动力学，研究了三种类型的半乳糖苷键的转糖基化和水解。我们估计了1,2-和1,3-键之间的过渡态自由能差（DeltaDeltaG（double dagger）0值等于5.34 +/- 0.85 kJ / mol）和1,6-键和1，之间 在由TmGal36A催化的反应过程中，pNP-半乳糖苷中有3个键（DeltaDeltaG（双匕首）0 = 1.46 +/- 0.23 kJ / mol）。利用自由能差形成和水解糖苷键（DeltaDeltaG（双匕首）F-DeltaDeltaG（双匕首）H），我们发现1
• Methods and formulations for reducing circulating antibodies
  申请人：——

  公开号：US20010010818A1

  公开（公告）日：2001-08-02

  The invention provides methods for reducing circulating levels of antibodies, particularly disease-associated antibodies. The methods entail administering effective amounts of epitope-presenting carriers to an individual. In other embodiments, ex vivo methods for reducing circulating levels of antibodies are provided which employ epitope-presenting carriers.

  本发明提供了降低循环抗体水平的方法，特别是疾病相关抗体。该方法包括向个体施用有效剂量的表位呈现载体。在其他实施例中，本发明提供了利用表位呈现载体的体外降低循环抗体水平的方法。
• Characterization of Properties and Transglycosylation Abilities of Recombinant α-Galactosidase from Cold-Adapted Marine Bacterium Pseudoalteromonas KMM 701 and Its C494N and D451A Mutants
  作者：Irina Bakunina、Lubov Slepchenko、Stanislav Anastyuk、Vladimir Isakov、Galina Likhatskaya、Natalya Kim、Liudmila Tekutyeva、Oksana Son、Larissa Balabanova

  DOI：10.3390/md16100349

  日期：——

  (α-PsGal) from the cold-adapted marine bacterium Pseudoalteromonas sp. KMM 701, and its mutants D451A and C494N, were studied in terms of their structural, physicochemical, and catalytic properties. Homology models of the three-dimensional α-PsGal structure, its active center, and complexes with D-galactose were constructed for identification of functionally important amino acid residues in the active site

  一种新的野生型重组冷活性α-d-半乳糖苷酶（α-PsGal），来自适应寒冷的海洋细菌Pseudoalteromonas sp。研究了KMM 701及其突变体D451A和C494N的结构，物理化学和催化特性。建立了三维α-PsGal结构，其活性中心以及与D-半乳糖的复合物的同源性模型，以利用酶的α-半乳糖苷酶的晶体结构鉴定酶活性位点中功能上重要的氨基酸残基。嗜酸乳杆菌为模板。野生α-PsGal和突变体C494N的圆二色性光谱大致相同。C494N突变降低了保留酶与标准对硝基苯基-α-吡喃半乳糖苷（pNP-α-Gal）亲和力的效率。薄层色谱法，使用基质辅助激光解吸/电离质谱法和核磁共振波谱法鉴定反应混合物中的糖基转移产物。α-PsGal具有狭窄的受体特异性。果糖，木糖，岩藻糖和葡萄糖在转糖基化反应中作为受体没有活性。α-PsGal由蜜三糖以及-α（1→6）-和-α（1→3）连接的对硝基苯基-合成
• Conjugates comprising galactose alpha 1,3 galactosyl epitopes and methods of using same
  申请人：——

  公开号：US20020160964A1

  公开（公告）日：2002-10-31

  This invention provides conjugates useful for xenotransplantation which comprise a galactose &agr;1,3 galactosyl (&agr;Gal) epitope conjugated to a valency platform molecule, preferably a chemically defined valency platform molecule which allows precise valency. The invention also provides compositions comprising these conjugates, and methods (such as methods for inducing tolerance) using these conjugates and compositions.

  该发明提供了用于异种移植的共轭物，其包括将半乳糖α1,3半乳糖基（αGal表位）与价数平台分子结合而成，优选为化学定义的价数平台分子，以允许精确的价数。该发明还提供了包括这些共轭物的组合物，以及使用这些共轭物和组合物的方法（例如诱导耐受的方法）。
• Bacteria targeted by human natural antibodies using α-gal conjugated receptor-specific glycopolymers
  作者：Jun Li、Sima Zacharek、Xi Chen、Jianqiang Wang、Wei Zhang、Adam Janczuk、Peng George Wang

  DOI：10.1016/s0968-0896(99)00099-1

  日期：1999.8

  Synthesis of polymerizable beta-lactosyl, Gal alpha 1-->3Gal and alpha-mannosyl acrylamide derivatives with either a hydrophobic aromatic spacer or a hydrophilic biocompatible oligoethoxyl spacer was accomplished. Radical terpolymerizations of beta-lactosyl monomer, alpha-mannosyl monomer, and acrylamide were conducted in aqueous media with ammonium persulfate and N,N,N,N'-tetramethylethylenediamine as initiators. The resulting water soluble glycopolymers were further transformed efficiently by a recombinant alpha 1-->3 galactosyltransferase to afford mediators bearing Gal alpha 1-->3Gal termini as xenoactive antigens and alpha-mannosyl termini as specific ligands for bacterial cells. The binding of the resulting multivalent glycopolymer to bacteria was tested by its ability to inhibit agglutination of yeast to E. coli. The binding of human natural anti-Gal antibodies to the alpha-Gal containing glycopolymers and a monovalent alpha-Gal-Man glycoconjugate was demonstrated by an ELISA inhibition assay. (C) 1999 Elsevier Science Ltd. All rights reserved.