6-O-β-D-galactopyranosyl-D-galactose | 3031-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-β-D-galactopyranosyl-D-galactose
• 英文别名: β-D-Galp-(1-> 6)-αβ-D-Galp；β-D-galactopyranosyl-(1-> 6)-D-galactose；β-D-galactopyranosyl-(1→6)-D-galactopyranose；Galβ1-6Gal；Galβ1→6Gal；Gal-β(1->6)-Gal；D-Galp-(1->6)-D-Gal；6-O-beta-D-galactopyranosyl-D-galactopyranose；(3R,4S,5R,6R)-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 3031-35-4
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: DLRVVLDZNNYCBX-JZSVMVJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-β-D-galactopyranosyl-D-galactose 在 glycoside hydrolase 42 enzyme Bga₄₂A from Bifidobacterium longum subsp. infantis ATCC 15697 、 sodium citrate 作用下， 反应 1.5h， 生成 D-吡喃葡萄糖
  参考文献：
  名称：

  Distinct substrate specificities of three glycoside hydrolase family 42  -galactosidases from Bifidobacterium longum subsp. infantis ATCC 15697

  摘要：

  糖苷水解酶家族 42（GH42）包括β-半乳糖苷酶，可催化从不同β-d-半乳糖苷的非还原端释放半乳糖（Gal）。促进健康的益生菌双歧杆菌是人体胃肠道微生物群的重要成员，它们产生的 GH42 酶能利用β-半乳糖苷发挥益生作用。然而，人们对单个 GH42 酶在底物单糖组成、糖苷键和聚合度方面的特异性还缺乏深入了解。对类似于各种牛奶和植物半乳寡糖的天然和合成底物进行动力学分析，区分了益生菌 B. longum subsp. infantis ATCC 15697 编码的三个 GH42 成员 Bga42A、Bga42B 和 Bga42C，并发现位点 +1 上的糖基残基及其与位点 -1 上末端 Gal 的连接是决定特异性的关键因素。因此，Bga42A 更喜欢母乳中的β1-3-半乳糖苷连接，以及其他葡萄糖或 Gal 位于位点 +1 上的β1-3-和β1-6-半乳糖苷。相反，Bga42B 能非常有效地水解 4-半乳糖苷（Galβ1-4Galβ1-4Glc）以及 4-半乳糖双糖（Galβ1-4Gal）和 4-半乳糖三糖（Galβ1-4Galβ1-4Gal）。Bga42C 的特异性与 Bga42B 相似，但活性低一个数量级。根据酶动力学、基因组织和系统发育分析，Bga42C 被认为参与了阿拉伯半乳聚糖衍生寡糖的代谢。三种 GH42 酶的不同动力学特征与 GH42 系统发育树中表示特定支系的独特序列基序相关联，为了解 GH42 亚特异性提供了新的视角。总之，这些数据说明了双歧杆菌对富含β-半乳糖苷的肠道生态位的代谢适应性，并强调了β-半乳糖苷代谢在益生双歧杆菌中的重要性和多样性。

  DOI：

  10.1093/glycob/cwt104
• 作为产物：
  描述：

  尾-D-Galactoside,2-nitrophenyl(9CI) 在 β-galactosidase from E. coli 、 3-O-methyl Glc 作用下， 以 various solvent(s) 为溶剂， 反应 48.0h， 以5.9%的产率得到6-O-β-D-galactopyranosyl-D-galactose
  参考文献：
  名称：

  有机溶剂对β-半乳糖苷酶合成半乳糖二糖的影响

  摘要：

  摘要通过五个不同来源的β-半乳糖苷酶通过转糖基化反应合成3-O-甲基异乳糖，N-乙酰乳糖胺，N-乙酰异乳糖胺和Gal（β1-6）Gal。产物的产量和分布取决于酶的来源和反应条件，即。添加的有机助溶剂的性质。在水性缓冲液中用E的β-半乳糖苷酶获得3-O-甲基异乳糖（47％），Gal（β1-6）Gal（6％），N-乙酰基异乳糖胺（30％）的产率。大肠杆菌。在与水混溶的有机溶剂存在下，相同的反应以低得多的速率发生。但是，对于脆弱拟杆菌和米曲霉的β-半乳糖苷酶，上述二糖的合成仅在有机溶剂（60％v / v磷酸三乙酯，磷酸三甲酯或四甘醇二甲醚），但不在缓冲水溶液中。在掺入有机溶剂的系统中，肺炎衣原体和圆环芽孢杆菌的β-半乳糖苷酶可产生3-O-甲基异乳糖和N-乙酰基乳糖胺，收率为30-40％。制备规模上的低聚糖的直接分离可以通过Ca 2+-配体交换色谱来实现。超滤还用于有效回收酶。

  DOI：

  10.1016/s0008-6215(97)00182-1

文献信息

• Fluorous-Assisted One-Pot Oligosaccharide Synthesis
  作者：Bo Yang、Yuqing Jing、Xuefei Huang

  DOI：10.1002/ejoc.200901155

  日期：2010.3

  A new method for oligosaccharide assembly that combines the advantages of one-pot synthesis and fluorous separation is described. After one-pot glycosylations are completed, a fluorous tag is introduced into the reaction mixture to selectively "catch" the desired oligosaccharide, which is rapidly separated from non-fluorous impurities by fluorous solid-phase extraction (F-SPE). Subsequent "release"

  描述了一种结合了一锅法合成和氟分离优势的寡糖组装新方法。一锅糖基化完成后，将氟标签引入反应混合物中，以选择性地“捕获”所需的寡糖，该寡糖可通过氟固相萃取（F-SPE）与非氟杂质快速分离。氟标签和F-SPE的随后“释放”无需使用费时和溶剂的硅胶色谱即可实现所需寡糖的纯化。线性和支链低聚糖已通过这种方法在短短几个小时内合成（用于整个低聚糖的组装和纯化过程）。
• Protein particles for therapeutic and diagnostic use
  申请人：——

  公开号：US20020142046A1

  公开（公告）日：2002-10-03

  Albumin particles in the nanometer and micrometer size range in an aqueous suspension are rendered stable against resolubilization without the aid of a cross-linking agent and witout denaturation, by the incorporation of a stabilizing agent in the particle composition. Stabilizing agents disclosed include reducing agents, oxdizing agents, hydrogen-accepting molecules, high molecular weight polymers, and sulfur-containing ring compounds. Also disclosed are fibrinogen-coated particles, cross-linked or non-cross-linked, and their use as co-aggregants with platelets and with themselves for purposes of shortening bleeding time and enhancing the effect of thrombin.

  通过在颗粒组合物中加入稳定剂，可使水悬浮液中纳米和微米大小的白蛋白颗粒在不借助交联剂和不发生变性的情况下稳定地防止溶解。已公开的稳定剂包括还原剂、氧化剂、氢接受分子、高分子量聚合物和含硫环化合物。此外，还公开了交联或非交联的纤维蛋白原涂层微粒，以及它们作为与血小板和自身的共聚物的用途，以达到缩短出血时间和增强凝血酶效果的目的。
• Scope and limitation of the application of the (methoxydimethyl)methyl group in the synthesis of 2′-O-, 6′-O- and 2′,6′-di-O-(α-l-arabinofuranosyl)-β-d-galactopyranosyl-(1→6)-d-galactoses
  作者：Anikó Borbás、Lóránt Jánossy、András Lipták

  DOI：10.1016/s0008-6215(99)00094-4

  日期：1999.5

  For the characterisation of the anticipated epitope of an arabinogalactan, isolated from the extract of Echinacea purpurea, the trisaccharide alpha-L-Araf-(1 --> 2)-beta-D-Galp-(1 --> 6)-D-Gal was synthesized. The easily available 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-beta-D-galactopyranosyl- (1 --> 6)-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose having the OH-2' free served as aglycone upon direct arabinosylation at the 2' position under Helferich conditions. The formed HgBr2 cleaved the acid sensitive protecting group at position 6', but under basic conditions the desired, fully protected trisaccharide, or its symmetrical dimerization derivative linked 6'- to 6'-position via an isopropylidene bridge, could be obtained. An alternative route involved arabinosylation of a hepta-O-acetylated digalactose with free OH-2'. Two other oligosaccharides, namely, alpha-L-Araf-(1 --> 6)-beta-D-Galp-(1 --> 6)-D-Gal and (alpha-L-Araf)(2)-(1 --> 2,6)-beta-D-Galp-(1 --> 6)-D-Gal were also synthesized and characterised. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of Model Compounds Related to Linear β-D-(1→6)-Galactosyl Side-Chains of Polysaccharides from Astragalus mongholicus Bunge
  作者：Fumiyuki Kiuchi、Noriyasu Hada、Ryo Shimura、Kyoko Hakamata、Hiroaki Kiyohara、Haruki Yamada、Tadahiro Takeda

  DOI：10.3987/com-14-s(k)61

  日期：——

  Stereocontrolled efficient syntheses of beta-(1 -> 6)-linked di-, tetra- and octa-galactans as model compounds of arabino-3,6-galactans isolated from Astragalus mongholicus are described. The syntheses consisted of simple glycosylation cycles: an acceptor and a donor prepared from a common compound were coupled, and the glycosylation product was converted to the acceptor and donor of the next glycosylation.
• Production of Galacto-oligosaccharides by the β-Galactosidase from Kluyveromyces lactis: Comparative Analysis of Permeabilized Cells versus Soluble Enzyme
  作者：Barbara Rodriguez-Colinas、Miguel A. de Abreu、Lucia Fernandez-Arrojo、Roseri de Beer、Ana Poveda、Jesus Jimenez-Barbero、Dietmar Haltrich、Antonio O. Ballesteros Olmo、Maria Fernandez-Lobato、Francisco J. Plou

  DOI：10.1021/jf2022012

  日期：2011.10.12

  The transgalactosylation activity of Kluyveromyces lactis cells was studied in detail. Cells were permeabilized with ethanol and further lyophilized to facilitate the transit of substrates and products. The resulting biocatalyst was assayed for the synthesis of galacto-oligosaccharides (GOS) and compared with two soluble beta-galactosidases from K. lactis (Lactozym 3000 L HP G and Maxilact LGX 5000). Using 400 g/L lactose, the maximum GOS yield, measured by HPAEC-PAD analysis, was 177 g/L (44% w/w of total carbohydrates). The major products synthesized were the disaccharides 6-galactobiose [Gal-beta(1 -> 6)-Gal] and allolactose [Gal-beta(1 -> 6)-Glc], as well as the trisaccharide 6-galactosyl-lactose [Gal-beta(1 -> 6)-Gal-beta(1 -> 4)-Glc], which was characterized by MS and 2D NMR. Structural characterization of another synthesized disaccharide, Gal-beta(1 -> 3)-Glc, was carried out. GOS yield obtained with soluble beta-galactosidases was slightly lower (160 g/L for Lactozym 3000 L HP G and 154 g/L for Maxilact LGX 5000); however, the typical profile with a maximum GOS concentration followed by partial hydrolysis of the newly formed oligosaccharides was not observed with the soluble enzymes. Results were correlated with the higher stability of beta-galactosidase when permeabilized whole cells were used.