benzyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: Gal(a1-4)Gal(b1-4)Glc(b)-O-Bn；(2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₅H₃₈O₁₆
• 分子量: 594.567
• InChiKey: MHJLZPNUWVYFMR-VAAZCZNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 苄基4-O-(3,4-O-异亚丙基己糖吡喃糖苷)吡喃己糖苷 在 α(1->4) galactotransferase 、 GAlE epimerase 、 manganese(ll) chloride 作用下， 反应 48.0h， 以76%的产率得到benzyl α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  寡糖的大规模酶法合成和新颖的纯化工艺

  摘要：

  在此，我们报告了三糖以及 iGb3 和 Gb3 衍生物的实用化学酶法合成，以及使用固定化酵母从反应混合物中去除单糖的新颖纯化工艺。大规模实现了高纯度寡糖化合物。这项研究代表了寡糖的简便酶法合成和新颖的纯化方法。

  DOI：

  10.1016/j.bmcl.2010.11.011

文献信息

• Sugar Nucleotide Regeneration Beads (Superbeads):  A Versatile Tool for the Practical Synthesis of Oligosaccharides
  作者：Xi Chen、Jianwen Fang、Jianbo Zhang、Ziye Liu、Jun Shao、Przemyslaw Kowal、Peter Andreana、Peng George Wang

  DOI：10.1021/ja005738v

  日期：2001.3.1

  Peng George Wang* Department of Chemistry, Wayne State Uni Versity Detroit, Michigan 48202 Recei Ved October 27, 2000 Application of carbohydrates in modern medicine is limited by the high cost of synthesis of most biologically important glycoconjugates. It is generally recognized that glycosyltransferasecatalyzed glycosylation is one of the most practical approaches. 1

  Xi Chen、Jianwen Fang、Jianbo Zhang、Ziye Liu、Jun Shao、Przemyslaw Kowal、Peter Andreana 和 Peng George Wang* 密歇根州底特律韦恩州立大学化学系 48202 接收日期 2000 年 10 月 27 日 碳水化合物在现代医学中的应用受到大多数生物学上重要的糖缀合物的高成本合成的限制。人们普遍认为糖基转移酶催化的糖基化是最实用的方法之一。1
• 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。
• 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.
• Large scale enzymatic synthesis of oligosaccharides and a novel purification process
  作者：Guangyan Zhou、Xianwei Liu、Doris Su、Lei Li、Min Xiao、Peng G. Wang

  DOI：10.1016/j.bmcl.2010.11.011

  日期：2011.1

  Herein we report the practical chemo enzymatic synthesis of trisaccharide and derivatives of iGb3 and Gb3, and a novel purification process using immobilized yeast to remove the monosaccharide from the reaction mixture. High purity oligosaccharide compounds were achieved in large scale. This study represents a facile enzymatic synthesis of and novel purification process of oligosaccharide.

  在此，我们报告了三糖以及 iGb3 和 Gb3 衍生物的实用化学酶法合成，以及使用固定化酵母从反应混合物中去除单糖的新颖纯化工艺。大规模实现了高纯度寡糖化合物。这项研究代表了寡糖的简便酶法合成和新颖的纯化方法。