6-O-alpha-D-吡喃半乳糖基-D-葡萄糖 | 13299-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-O-alpha-D-吡喃半乳糖基-D-葡萄糖
• 英文名称: melibiose
• 英文别名: α-melibiose；α-D-melibiose；6-O-Alpha-D-Galactopyranosyl-Alpha-D-Glucopyranose；(2S,3R,4S,5S,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 13299-20-2
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: DLRVVLDZNNYCBX-CQHUIXDMSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  86.0 °C
• 溶解度：
  1000.0 mg/mL

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-alpha-D-吡喃半乳糖基-D-葡萄糖 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 40.0 ℃ 、900.02 kPa 条件下， 反应 92.0h， 生成
  参考文献：
  名称：

  Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an α,ω-diamino-(oxa)alkyl spacer

  摘要：

  Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic bolaform amphiphiles with identical headgroups and alpha,omega-diamino-(oxa) alkyl spacers were synthesized by reductive aminations involving alpha,omega-diaminoalkanes and the appropriate sugars or aldehydes. The bolaform compounds were used as starting materials for the synthesis of the corresponding reduced-sugar based gemini surfactants in a reductive alkylation reaction employing a polymer-bound cyanoborohydride. A series of new gemini surfactants have been synthesized and characterized. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.023
• 作为产物：
  描述：

  棉子糖 在 recombinant Erwinia amylovora levansucrase 作用下， 以 aq. phosphate buffer 为溶剂， 反应 4.0h， 生成 D-果糖 、 6-O-alpha-D-吡喃半乳糖基-D-葡萄糖
  参考文献：
  名称：

  Biomolecular Characterization of the Levansucrase of Erwinia amylovora, a Promising Biocatalyst for the Synthesis of Fructooligosaccharides

  摘要：

  Erwinia amylovora is a plant pathogen that affects Rosaceae, such as apple and pear. In E. amylovora the fructans, produced by the action of a levansucrase (EaLsc), play a role in virulence and biofilm formation. Fructans are bioactive compounds, displaying health-promoting properties in their own right. Their use as food and feed supplements is increasing. In this study, we investigated the biomolecular properties of EaLsc using HPAEC-PAD, MALDI-TOF MS, and spectrophotometric assays. The enzyme, which was heterologously expressed in Escherichia coli in high yield, was shown to produce mainly fructooligosaccharides (FOSs) with a degree of polymerization between 3 and 6. The kinetic properties of EaLsc were similar to those of other phylogenetically related Gram-negative bacteria, but the good yield of FOSs, the product spectrum, and the straightforward production of the enzyme suggest that EaLsc is an interesting biocatalyst for future studies aimed at producing tailor-made fructans.

  DOI：

  10.1021/jf4023178

文献信息

• Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis
  作者：Richard Daniellou、Christopher P. Phenix、Pui Hang Tam、Michael C. Laliberte、David R. J. Palmer

  DOI：10.1039/b417757f

  日期：——

  Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.

  来自枯草芽孢杆菌的肌醇脱氢酶（EC 1.1.1.18）显示出在活性位点旁有一个非极性腔，使得保护的消旋肌醇衍生物如4-O-苯甲基-myoinositol能够以非常高的表观立体选择性被识别。
• Method for Treating Abnormal Polyglutamine-Mediated Disease
  申请人：NATIONAL TAIWAN NORMAL UNIVERSITY

  公开号：US20150025028A1

  公开（公告）日：2015-01-22

  A method for treating an abnormal polyglutamine-mediated disease is disclosed, which comprises: administering a pharmaceutical composition comprising a trehalose-based compound to a subject in need. Additionally, the pharmaceutical composition optionally further comprises a trehalase inhibitor.

  揭示了一种治疗异常多谷氨酰基介导疾病的方法，包括：向需要的受试者投予包含以海藻糖为基础的化合物的药物组合物。此外，该药物组合物还可以选择性地进一步包含一种海藻糖酶抑制剂。
• 6'-(1-Adamanta
  申请人：American Cyanamid Company

  公开号：US04359460A1

  公开（公告）日：1982-11-16

  6'-(1-Adamantanecarboxylate)-6-O-.alpha.-D-galactopyranosyl-.alpha.-D-gluco pyranose sulfate salts, useful as complement inhibitors, and the process for making such compounds.

  6'-(1-Adamantanecarboxylate)-6-O-.alpha.-D-galactopyranosyl-.alpha.-D-gluco pyranose硫酸盐是一种有用的补体抑制剂，制备此类化合物的方法。
• Indium-mediated C-allylation of melibiose
  作者：Christian Denner、Manuel Gintner、Hanspeter Kählig、Walther Schmid

  DOI：10.3762/bjoc.15.238

  日期：——

  The indium-mediated allylation reaction has been applied to melibiose, a disaccharidic substrate. This elongation methodology allows for a short, efficient and diastereoselective approach towards complex glycosylated carbohydrate structures. The stereochemical outcome of the key intermediates, allylated disaccharides, has been determined by X-ray analysis. Ozonolysis of the introduced double bond yielded

  铟介导的烯丙基化反应已应用于蜜二糖（一种糖质底物）。这种延长方法学允许对复杂的糖基化碳水化合物结构进行简短，有效和非对映选择性的方法。关键中间体烯丙基化二糖的立体化学结果已通过X射线分析确定。引入的双键的臭氧分解分别在吡喃类化合物和两种异头异构体形式的呋喃类异构体的平衡中产生未保护的伸长的二糖。Per- ø -acetylation已经执行，以促进结构鉴定的异构体混合物的分离。主要产物显示在二糖的还原端采用伸长单元的β-吡喃酮形式。
• Non-Natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant Gp120
  作者：Katherine D McReynolds、Abhijit Bhat、John C Conboy、S.Scott Saavedra、Jacquelyn Gervay-Hague

  DOI：10.1016/s0968-0896(01)00325-x

  日期：2002.3

  Interactions of recombinant gp120 (rgp120) with non-natural glycosphingolipids (GSLs) and structurally simpler analogues have been studied using a competitive adhesion assay. Conjugates of cellobiosyl ceramide and melibiosyl ceramide were synthetically prepared as water-soluble GSL analogues. These ligands were screened against a panel of biologically relevant analogues, and the results show that their interactions with rgp120 are comparable to natural cellular receptors. Glycolipid interactions with rgp120 were probed further by the synthesis and testing of structurally simpler analogues that were obtained by reductive amination of lactose, cellobiose, and melibiose with a biotinylated amino ethylene glycol moiety. RGp120 did not recognize conjugates lacking a lipid component. However. palmitoylation of the secondary amino alditols yielded compounds with comparable rgp120 affinity to the natural cellular receptor. galactosyl ceramide (GalCer). Taken together, the SAR showed that both a hydrophobic and it hydrophilic component are required for rgp120 recognition. Moreover. structural variability in the carbohydrate headgroup did not significantly alter rgp120 recognition indicating that this interaction is not highly specific. (C) 2002 Elsevier Science Ltd. All rights reserved.