3-O-(β-D-galactopyranosyl)-D-arabinose | 61272-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(β-D-galactopyranosyl)-D-arabinose
• 英文别名: 3-O-β-D-galactopyranosyl-D-arabinose；galarose；Gal(b1-3)D-Araf；(2S,3R,4S,5R,6R)-2-[(2R,3S,4S)-4,5-dihydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 61272-23-9；130767-77-0；130767-78-1
• 化学式: C₁₁H₂₀O₁₀
• 分子量: 312.274
• InChiKey: YNHLBDYXAQJXAN-VGRCRPPNSA-N

物化性质

• 沸点：
  634.5±55.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  21
• 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：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-(β-D-galactopyranosyl)-D-arabinose 在 Pd-BaSO₄ 盐酸 、 氢气 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 25.9h， 生成
  参考文献：
  名称：

  Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine

  摘要：

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00294-4
• 作为产物：
  描述：

  Lactose 在 sodium hydroxide 、 双氧水 、 硼酸 作用下， 以 水 为溶剂， 反应 2.0h， 以60%的产率得到3-O-(β-D-galactopyranosyl)-D-arabinose
  参考文献：
  名称：

  以硼酸盐为催化剂和保护基的过氧化氢对单糖和二糖的选择性碱性氧化降解

  摘要：

  乳糖，麦芽糖，纤维二糖和半乳糖可在硼酸盐存在下被H2O2一步选择性地高产率地降解为相应的下一个较低的醛糖和甲酸。当添加少量的EDTA时，选择性进一步提高，以抑制过渡金属离子的影响，该过渡金属离子通过自由基途径催化H2O2的分解，导致醛糖的非选择性氧化降解。硼酸盐在醛糖的选择性氧化降解中的作用是双重的：催化起始醛糖的降解和保护下一个较低醛糖免于氧化。

  DOI：

  10.1016/0008-6215(94)00282-k

文献信息

• 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。
• Berg, Ron van den; Peters, Joop A.; Bekkum, Herman van, Journal of the Chemical Society. Perkin transactions I, 1994, # 9, p. 1117 - 1118
  作者：Berg, Ron van den、Peters, Joop A.、Bekkum, Herman van

  DOI：——

  日期：——
• Regeneration of Free Reducing Glycans from Reductive Amination-Tagged Glycans by Oxone
  作者：Qing Zhang、Shuaishuai Wang、Zhonghua Li、Yi Lasanajak、Lei Li、Xuezheng Song

  DOI：10.1021/acs.joc.1c02709

  日期：2022.3.4
• An improved procedure for the methylation analysis of oligosaccharides and polysaccharides
  作者：Philip J. Harris、Robert J. Henry、Anthony B. Blakeney、Bruce A. Stone

  DOI：10.1016/0008-6215(84)85106-x

  日期：1984.4

  An improved procedure for the methylation analysis of oligosaccharides and polysaccharides is described. Steps in the procedure were examined and optimised for quantitative recovery and speed. Methylation was shown to be complete by using [14C]methyl iodide. All operations were performed in the same tube and the need to concentrate solutions containing acetylated alditols of methylated sugars was eliminated, thus minimising losses due to volatilization. The method is convenient, gives high recoveries of acetylated alditols of methylated sugars, and allows analysis of the glycosyl linkages of oligo- or poly-saccharides to be completed within a working day. A wide range of oligo- and poly-saccharides were methylated by this procedure.
• Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine
  作者：Gerhard Kretzschmar、Wilhelm Stahl

  DOI：10.1016/s0040-4020(98)00294-4

  日期：1998.6

  The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.