4-O-β-D-吡喃半乳糖基-D-半乳吡喃糖 | 2152-98-9

• 物质功能分类: 生物化工 - 糖类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-O-β-D-吡喃半乳糖基-D-半乳吡喃糖
• 中文别名: 4-Β-半乳二糖
• 英文名称: β-D-galactopyranosyl-(1→4)-D-galactopyranose
• 英文别名: 4-O-β-D-galactopyranosyl-D-galactopyranose；(1<*>4)-α-D-galactobiose；1,4-β-D-galactobiose；β-1,4-galactobiose；4-galactobiose；galactobiose；beta-D-galactopyranosyl-(1->4)-D-galactopyranose；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3R,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 2152-98-9
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: GUBGYTABKSRVRQ-HEJLOQJISA-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

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  4-O-β-D-吡喃半乳糖基-D-半乳吡喃糖 在 哌啶 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 51.5h， 生成 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-D-galactopyranose
  参考文献：
  名称：

  诱导过敏的四糖“ 4P-X”的合成

  摘要：

  包括4P-X（β-D-吡喃半乳糖-（1→4）-β-D-吡喃半乳糖-（1→6）-[β-D-吡喃半乳糖-（1→4）]-β-D-吡喃葡萄糖）圆环芽孢杆菌衍生的β-半乳糖苷酶产生的半乳糖寡糖（GOS）中的“糖”。已知4P-X会引起特别强烈的过敏。高纯度4P-X对于用作定量GOS中4P-X量的标准品至关重要。但是，从未报道过高纯度4P-X的分离。在这项研究中，我们在短时间内通过有机和酶促化学合成的组合实现了4P-X的合成。这是分离的高纯度4P-X的首次报道。

  DOI：

  10.1016/j.carres.2016.11.013
• 作为产物：
  描述：

  2,4-dinitrophenyl 1,4-β-D-galactobioside 在 水 作用下， 生成 4-O-β-D-吡喃半乳糖基-D-半乳吡喃糖
  参考文献：
  名称：

  Activity of three β-1,4-galactanases on small chromogenic substrates

  摘要：

  beta-1,4-Galactanases belong to glycoside hydrolase family GH 53 and degrade galactan and arabinogalactan side chains of the complex pectin network in plant cell walls. Two fungal beta-1,4-galactanases from Aspergillus aculeatus, Meripileus giganteus and one bacterial enzyme from Bacillus licheniformis have been kinetically characterized using the chromogenic substrate analog 4-nitrophenyl beta-1,4-D-thiogalactobioside synthesized by the thioglycoligase approach. Values of k(cat)/K-m for this substrate with A. aculeatus beta-1,4-galactanase at pH 4.4 and for M. giganteus beta-1,4-galactanase at pH 5.5 are 333 M (1) s (1) and 62 M (1) s (1), respectively. By contrast the B. licheniformis beta-1,4-galactanase did not hydrolyze 4-nitrophenyl beta-1,4-D-thiogalactobioside. The different kinetic behavior observed between the two fungal and the bacterial beta-1,4-galactanases can be ascribed to an especially long loop 8 observed only in the structure of B. licheniformis beta-1,4-galactanase. This loop contains substrate binding subsites -3 and -4, which presumably cause B. licheniformis beta-1,4-galactanase to bind 4-nitrophenyl -1,4-beta-D-thiogalactobioside non-productively. In addition to their cleavage of 4-nitrophenyl -1,4-beta-D-thiogalactobioside, the two fungal enzymes also cleaved the commercially available 2-nitrophenyl-1,4-beta-D-galactopyranoside, but kinetic parameters could not be determined because of transglycosylation at substrate concentrations above 4 mM. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.017

文献信息

• Distinct substrate specificities of three glycoside hydrolase family 42  -galactosidases from Bifidobacterium longum subsp. infantis ATCC 15697
  作者：A. H. Viborg、T. Katayama、M. Abou Hachem、M. C. Andersen、M. Nishimoto、M. H. Clausen、T. Urashima、B. Svensson、M. Kitaoka

  DOI：10.1093/glycob/cwt104

  日期：2014.2.1

  Glycoside hydrolase family 42 (GH42) includes β-galactosidases catalyzing the release of galactose (Gal) from the non-reducing end of different β-d-galactosides. Health-promoting probiotic bifidobacteria, which are important members of the human gastrointestinal tract microbiota, produce GH42 enzymes enabling utilization of β-galactosides exerting prebiotic effects. However, insight into the specificity of individual GH42 enzymes with respect to substrate monosaccharide composition, glycosidic linkage and degree of polymerization is lagging. Kinetic analysis of natural and synthetic substrates resembling various milk and plant galactooligosaccharides distinguishes the three GH42 members, Bga42A, Bga42B and Bga42C, encoded by the probiotic B. longum subsp. infantis ATCC 15697 and revealed the glycosyl residue at subsite +1 and its linkage to the terminal Gal at subsite −1 to be key specificity determinants. Bga42A thus prefers the β1-3-galactosidic linkage from human milk and other β1-3- and β1-6-galactosides with glucose or Gal situated at subsite +1. In contrast, Bga42B very efficiently hydrolyses 4-galactosyllactose (Galβ1-4Galβ1-4Glc) as well as 4-galactobiose (Galβ1-4Gal) and 4-galactotriose (Galβ1-4Galβ1-4Gal). The specificity of Bga42C resembles that of Bga42B, but the activity was one order of magnitude lower. Based on enzyme kinetics, gene organization and phylogenetic analyses, Bga42C is proposed to act in the metabolism of arabinogalactan-derived oligosaccharides. The distinct kinetic signatures of the three GH42 enzymes correlate to unique sequence motifs denoting specific clades in a GH42 phylogenetic tree providing novel insight into GH42 subspecificities. Overall, the data illustrate the metabolic adaptation of bifidobacteria to the β-galactoside-rich gut niche and emphasize the importance and diversity of β-galactoside metabolism in probiotic bifidobacteria.

  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。
• ガラクトオリゴ糖の製造方法及びその中間体
  申请人：合同酒精株式会社

  公开号：JP2018030828A

  公开（公告）日：2018-03-01

  【課題】アレルギー反応を発症し得るガラクトオリゴ糖の製造方法及びその中間体の提供。【解決手段】式(５)のラクトース保護体の６位水酸基にガラクトビオース保護体の１位を付加した後、水酸基の保護基を脱保護する工程を含む一般式（１）で示されるガラクトオリゴ糖の製造方法。【選択図】図５

  题目：制造可能引起过敏反应的半乳糖寡糖的方法以及其中间体的提供。 解决方法：包括在式（5）的乳糖保护体的6位羟基上添加半乳糖保护体的1位，然后去除羟基的保护基的步骤，所示的一般式（1）的半乳糖寡糖的制造方法。 选择图：图5。
• Gram-scale chemical synthesis of galactosyllactoses and their impact on infant gut microbiota <i>in vitro</i>
  作者：Evy Meeusen、Linqiu Cao、Dianne J. Delsing、Andre Groeneveld、Margreet Heerikhuisen、Frank Schuren、Thomas J. Boltje

  DOI：10.1039/d3ob02069j

  日期：——

  We report the gram-scale chemical synthesis of 3′-, 4′-, and 6′-galactosyllactose starting from lactose. The impact of these galactosyllactoses on infant gut microbiota was tested in vitro by fermentation experiments using infant faecal samples.

  我们报告了从乳糖出发，以克为单位化学合成 3′-、4′- 和 6′-半乳糖的过程。我们利用婴儿粪便样本进行了发酵实验，在体外测试了这些半乳糖对婴儿肠道微生物群的影响。
• Label-Free, Real-Time Glycosyltransferase Assay Based on a Fluorescent Artificial Chemosensor
  作者：Jirarut Wongkongkatep、Yoshifumi Miyahara、Akio Ojida、Itaru Hamachi

  DOI：10.1002/anie.200503107

  日期：2006.1.16
• MEDIUM WITH A PLANT NON-METABOLIZABLE SUGAR FOR IMPROVING SEED GERMINATION
  申请人：WEYERHAEUSER NR COMPANY

  公开号：US20160081336A1

  公开（公告）日：2016-03-24

  What is described is a nutritive media for a manufactured seed comprising a plant non-metabolizable sugar and a manufactured seed comprising plant non-metabolizable sugar in its nutritive medium