β-D-Gal-(1->3)-D-AraOH | 20869-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-Gal-(1->3)-D-AraOH
• 英文别名: 3-O-β-D-galactopyranosyl-D-arabinose；β-Galp-(1->3)-Ara；β-D-Gal-(1<*>3)-D-Ara；3-O-β-galactopyranosyl-D-arabinose；3-O-β-D-Galactopyranosyl-arabinose；beta-D-Gal-(1->3)-D-Ara；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(3S,4R,5R)-2,3,5-trihydroxyoxan-4-yl]oxyoxane-3,4,5-triol
• CAS: 20869-30-1
• 化学式: C₁₁H₂₀O₁₀
• 分子量: 312.274
• InChiKey: XSXQXHMPBBNYRD-VGRCRPPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 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：

  β-D-Gal-(1->3)-D-AraOH 、 sodium,[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl [hydroxy-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphoryl] phosphate 在 UDP-galactose-4-epimerasae 、 manganese(ll) chloride 、 bovine serum albumin 作用下， 以 various solvent(s) 为溶剂， 反应 48.0h， 以77%的产率得到α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->3)-β-D-arabinopyranose
  参考文献：
  名称：

  Efficient chemoenzymatic synthesis of globotriose and its derivatives with a recombinant α-(1→4)-galactosyltransferase

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(02)00106-4
• 作为产物：
  描述：

  乳糖酸 在 氧气 、 lithium hydroxide 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以13.3 mg的产率得到β-D-Gal-(1->3)-D-AraOH
  参考文献：
  名称：

  Degradation of Unprotected Aldohexonic Acids to Aldopentoses Promoted by Light and Oxygen

  摘要：

  Herein reported is a photoredox-catalyzed oxidative degradation reaction of unprotected aldohexonic acids, which are shortened by one-carbon to the corresponding aldopentoses. Oxygen including aerial oxygen is used as a terminal oxidant. The mild reaction conditions permit even disaccharides to successfully undergo the degradation reaction with the glycosidic bond remaining intact. Quinic acid is also converted to a useful chiral synthetic intermediate.

  DOI：

  10.1246/cl.200517

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。
• Synthesis of N-acetyl-lactosamine via ozonolysis of a nitro derivative
  作者：Erika Lattová、Ladislav Petruš

  DOI：10.1016/0008-6215(92)80097-k

  日期：1992.11
• Degradation of Unprotected Aldohexonic Acids to Aldopentoses Promoted by Light and Oxygen
  作者：Yusuke Masuda、Misato Ito、Masahiro Murakami

  DOI：10.1246/cl.200517

  日期：2020.11.5

  Herein reported is a photoredox-catalyzed oxidative degradation reaction of unprotected aldohexonic acids, which are shortened by one-carbon to the corresponding aldopentoses. Oxygen including aerial oxygen is used as a terminal oxidant. The mild reaction conditions permit even disaccharides to successfully undergo the degradation reaction with the glycosidic bond remaining intact. Quinic acid is also converted to a useful chiral synthetic intermediate.
• 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.