甲基 4-O-吡喃半乳糖基吡喃半乳糖苷 | 80446-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基 4-O-吡喃半乳糖基吡喃半乳糖苷
• 中文别名: 甲基4-O-吡喃半乳糖基吡喃半乳糖苷；1,2,3-丙三基异十三八烷酸酯
• 英文名称: Methyl O-α-D-galactopyranosyl-(1->4)-β-D-galactopyranoside
• 英文别名: methyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranoside；Methyl 4-O-(α-D-galactopyranosyl)-β-D-galactopyranoside；methyl 4-O-α-D-galactopyranosyl-β-D-galactopyranoside；α-D-Gal-(1-4)-β-D-Gal-OMe；Galα4GalβOMe；methyl galabiose；Methyl 4-O-alpha-D-galactopyranosyl-beta-D-Galactopyranoside；(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 80446-84-0
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: FHNIYFZSHCGBPP-FUZIMHMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 甲基 4-O-吡喃半乳糖基吡喃半乳糖苷 在 吡啶 作用下， 以73%的产率得到methyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Application of the imidate procedure to α-d-galactosyltion

  摘要：

  DOI：

  10.1016/s0008-6215(00)81040-x
• 作为产物：
  描述：

  苯基2,3,4,6-四-O-苯甲基-1-硫代-Β-D-半乳糖皮蒽 在 palladium on activated charcoal 2,6-di-tert-butyl-methylpyridine 、 氢气 、 trifluoromethanesulfonic acid anhydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， -78.0~25.0 ℃ 、345.0 kPa 条件下， 反应 26.0h， 生成 甲基 4-O-吡喃半乳糖基吡喃半乳糖苷
  参考文献：
  名称：

  2,3,4,6-四-O-苄基-β-D-吡喃半乳糖基苯基亚砜作为糖基供体。合成一些含有α-D-吡喃半乳糖基的寡糖。

  摘要：

  DOI：

  10.1016/s0008-6215(00)90937-6

文献信息

• Preparation of α and β anomers of various isomeric methyl O-d-galactopyranosyl-d-galactopyranosides. Standards for interpretation of 13C-n.m.r. spectra of d-galactopyranans
  作者：Philip A.J. Gorin

  DOI：10.1016/s0008-6215(00)80790-9

  日期：1982.2

  r. resonances of α and β anomers of methyl O - d -galactopyranosyl-β- d -galactopyranosides. In terms of application of these shift values and those of related d -galactobioses to the structural analysis of d -galactopyranans by shift comparisons, some generalizations can be made. For β- d -galactopyranans, the resonances of glycosyloxylated carbon atoms of methyl O -β- d -galactopyranosyl-β- d -galactopyranosides

  摘要通过将2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物与适当的部分O-缩合制备甲基O-β-d-吡喃半乳糖基-β-d-吡喃半乳糖苷的四个异构体。甲基β-d-吡喃半乳糖苷的取代衍生物。在溴化汞的存在下，3,4,6-三-O-乙酰基-1,2-O-（1-乙氧基亚乙基）-α-d-吡喃半乳糖与相同的受体反应导致形成α和β β键。因此，有可能分配13个Cn.mr共振的甲基O-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷的α和β端基异构体。在通过移位比较将这些移位值和相关的d-半乳双歧杆菌的值应用于d-半乳糖吡喃聚糖的结构分析方面，可以做出一些概括。对于β-d-吡喃半乳糖，甲基O-β-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷的糖基氧基化碳原子的共振对结构敏感，并且似乎具有典型值，而随着C-1'信号的移位观察到有限的变化。另一方面，为了将结构分配给含有α键的d-吡喃半乳糖，甲基O-α-d-吡喃半乳糖基-
• Large-scale synthesis of globotriose derivatives through recombinant E. coli
  作者：Jianbo Zhang、Przemyslaw Kowal、Xi Chen、Peng George Wang

  DOI：10.1039/b304911f

  日期：——

  The carbohydrate chains decorating cell membranes and secreted proteins participate in a range of important biological processes. However, their ultimate significance and possible therapeutic potential have not been fully explored due to the lack of economical methods for their production. This study is an example of the use of a genetically engineered bacterial strain in the preparation of diverse oligosaccharides. Based on an ex vivo biosynthetic pathway, an artificial gene cluster was constructed by linking the genes of five associated enzymes on a plasmid vector. This plasmid was inserted into the E. coli NM522 strain to form globotriose-producing cells (‘superbug’ pLDR20-CKTUF). The specific strain was conveniently applied to the synthesis of globotriose trisaccharide and its derivatives, as potential neutralizers for Shiga toxin. This work demonstrates a novel and economical method for generating ligand diversity for carbohydrate drug development.

  装饰细胞膜和分泌蛋白的碳水化合物链参与一系列重要的生物过程。然而，由于缺乏经济的生产方法，它们的最终意义和可能的治疗潜力尚未得到充分探索。这项研究是使用基因工程菌株制备多种寡糖的一个例子。基于离体生物合成途径，通过将五种相关酶的基因连接在质粒载体上构建了人工基因簇。将该质粒插入大肠杆菌 NM522 菌株中，形成球三糖生产细胞（“超级细菌”pLDR20-CKTUF）。该特定菌株可方便地应用于球三糖三糖及其衍生物的合成，作为志贺毒素的潜在中和剂。这项工作展示了一种为碳水化合物药物开发产生配体多样性的新颖且经济的方法。
• Synthesis of di- and tri-saccharides corresponding to receptor structures recognised by pyelonephritogenic E. coli fimbriae (pili)
  作者：Per J. Garegg、Hans Hultberg

  DOI：10.1016/0008-6215(82)84007-x

  日期：1982.12

  Syntheses are described of di- and tri-saccharides required for studies of the inhibition of adhesion by means of fimbriae of pyelonephritogenic E. coli bacteria to epithelium cells in the urinary tract containing suitable receptor sites. The disaccharides are the rho-nitrophenyl and methyl glycosides of 4-omicron-alpha-D-galactopyranosyl-beta-D-galactopyranose, and the trisaccharides are the rho-nitrophenyl and methyl glycosides of 4-omicron-(4-omicron-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)-beta- D-glucopyranose. The key aglycons were the 1,2,3,6-tetrabenzoate of alpha-D-galactose and the 1,2,3,6,-2',3',6'-heptabenzoate of alpha-lactose. Glycosidations were performed with 2,3,4,6-tetra-omicron-benzyl-alpha-D-galactopyranosyl chloride as glycosylating agent and silver triflate as promoter.
• Efficient chemoenzymatic synthesis of globotriose and its derivatives with a recombinant α-(1→4)-galactosyltransferase
  作者：Jianbo Zhang、Przemyslaw Kowal、Jianwen Fang、Peter Andreana、Peng George Wang

  DOI：10.1016/s0008-6215(02)00106-4

  日期：2002.6

  A truncated alpha-(1-->4)-galactosyltransferase (LgtC) gene from Neisseria meningitidis was cloned. The recombinant glycosyltransferase was expressed in Escherichia coli BL21 (DE3) strain with high specific activity (5 units/mg protein). Its acceptor specificity was carefully characterized. Then the purified enzyme was utilized in highly efficient syntheses of globotriose and a variety of alpha-(1-->4)-galactosylated derivatives as potential antibacterial agents. (C) 2002 Published by Elsevier Science Ltd.
• Composition for therapeutic or diagnostic use
  申请人：Källenius, Gunilla Petterson

  公开号：EP0035484B1

  公开（公告）日：1984-08-22