(2-[2-(2-aminoethoxy)ethoxy]ethyl) β-D-galactopyranoside | 126765-29-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-[2-(2-aminoethoxy)ethoxy]ethyl) β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 126765-29-5
• 化学式: C₁₂H₂₅NO₈
• 分子量: 311.332
• InChiKey: DRRJZKOKUMEZCF-YBXAARCKSA-N

物化性质

• 沸点：
  530.9±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  144
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  exo-5-norbornene-2-carboxylic acid 、 (2-[2-(2-aminoethoxy)ethoxy]ethyl) β-D-galactopyranoside 在 N-羟基丁二酰亚胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (2-{2-[2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethyl)-amide
  参考文献：
  名称：

  Designed potent multivalent chemoattractants for Escherichia coli

  摘要：

  Bacterial chemotactic responses are initiated when certain small molecules (i.e., carbohydrates, amino acids) interact with bacterial chemoreceptors. Although bacterial chemotaxis has been the subject of intense investigations, few have explored the influence of attractant structure on signal generation and chemotaxis. Previously, we found that polymers bearing multiple copies of galactose interact with the chemoreceptor Trg via the periplasmic binding protein glucose/galactose binding protein (GGBP). These synthetic multivalent ligands were potent agonists of Escherichia coli chemotaxis. Here, we report on the development of a second generation of multivalent attractants that possess increased chemotactic activities. Strikingly, the new ligands can alter bacterial behavior at concentrations 10-fold lower than those required with the original displays; thus, they are some of the most potent synthetic chemoattractants known. The potency depends on the number of galactose moieties attached to the oligomer backbone and the length of the linker tethering these carbohydrates. Our investigations reveal the plasticity of GGBP; it can bind and mediate responses to several carbohydrates and carbohydrate derivatives. These attributes of GGBP may underlie the ability of bacteria to sense a variety of ligands with relatively few receptors. Our results provide insight into the design and development of compounds that can modulate bacterial chemotaxis and pathogenicity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00162-6
• 作为产物：
  描述：

  alpha-D-半乳糖 在 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 sodium acetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.58h， 生成 (2-[2-(2-aminoethoxy)ethoxy]ethyl) β-D-galactopyranoside
  参考文献：
  名称：

  合成凝集素对表面固定化碳水化合物的分子识别。

  摘要：

  碳水化合物和蛋白质的分子识别介导了广泛的生理过程，合成碳水化合物受体（“合成凝集素”）的发展构成了生物医学技术的关键进步。在这篇文章中，我们报告了一种合成凝集素，它选择性地与固定在分子单层中的碳水化合物结合。受我们之前工作的启发，我们制备了一种荧光标记的合成凝集素，由三肽 Cys-His-Cys 的环状二聚体组成，其通过单体的空气氧化自发形成。N-乙酰神经氨酸 (NANA)、β-D-半乳糖、β-D-葡萄糖和 α-D-甘露糖的胺系衍生物微接触印在环氧化物终止的自组装单层上。连续打印产生了两种碳水化合物的简单微阵列。通过在固定化碳水化合物上孵育来研究合成凝集素的选择性。通过荧光显微镜观察合成凝集素与固定化 NANA 和β-D-半乳糖的选择性结合。在竞争实验中筛选了合成凝集素的选择性和亲和力。此外，将合成凝集素的碳水化合物结合与凝集素伴刀豆球蛋白 A 和花生凝集素的碳水化合物结合进行了比较。发现

  DOI：

  10.3762/bjoc.10.138

文献信息

• Oligosaccharide-camptothecin conjugates as potential antineoplastic drugs: Design, synthesis and biological evaluation
  作者：Maolin Li、Wenchong Ye、Kaishuo Fu、Cui zhou、Yonghui Shi、Weiping Huang、Wenming Chen、Jiliang Hu、Zhilin Jiang、Wen Zhou

  DOI：10.1016/j.ejmech.2020.112509

  日期：2020.9

  Thirty novel 20 (S)-O-linked camptothecin (CPT) glycoconjugates were synthesized. They showed more potent in vitro cytotoxicities over irinotecan, but very weak direct topoisomerase I (Topo I) inhibition was observed at 100.0 μM. Oligosaccharide types, length of a PEG linker and acetyl groups exerted obvious effects on cytotoxicity, selectivity, water solubility and stability of the newly synthesized

  合成了三十种新颖的20（S）-O-连接的喜树碱（CPT）糖缀合物。他们表现出更有效的体外细胞毒性过伊立替康，但非常弱的直接拓扑异构酶I在100.0观察（TOPO I）抑制μ M.寡糖类型，PEG接头的长度和乙酰基作用于细胞毒性，选择性，水溶性明显影响，并新合成的CPT糖缀合物的稳定性。结构40与CPT相比，博来霉素（BLM）二糖与引入的酯部分中的二甘醇相连，具有更高的抗肿瘤活性和独特的选择性。静脉内动物急性毒性（160 mg / kg）未检测到毒性。总的来说，将具有靶向肿瘤的寡糖附着到CPT的20（S）-OH上可以为当前的Topo I毒药带来的艰巨问题提供解决方案。
• Szurmai, Zoltan; Szabo, Lajos; Liptak, Andras, Acta Chimica Hungarica, 1989, vol. 126, # 2, p. 259 - 270
  作者：Szurmai, Zoltan、Szabo, Lajos、Liptak, Andras

  DOI：——

  日期：——
• Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides
  作者：Na Kong、Manishkumar R. Shimpi、Jae Hyeung Park、Olof Ramström、Mingdi Yan

  DOI：10.1016/j.carres.2014.09.006

  日期：2015.3

  Carbohydrate-functionalized single-walled carbon nanotubes (SWNTs) were synthesized using microwave-assisted reaction of perfluorophenyl azide with the nanotubes. The results showed that microwave radiation provides a rapid and effective means to covalently attach carbohydrates to SWNTs, producing carbohydrate-SWNT conjugates for biorecognition. The carbohydrate-functionalized SWNTs were furthermore shown to interact specifically with cognate carbohydrate-specific proteins (lectins), resulting in predicted recognition patterns. The carbohydrate-presenting SWNTs constitute a new platform for sensitive protein-or cell recognition, which pave the way for glycoconjugated carbon nanomaterials in biorecognition applications. (C) 2014 Elsevier Ltd. All rights reserved.
• Designed potent multivalent chemoattractants for Escherichia coli
  作者：J Gestwicki

  DOI：10.1016/s0968-0896(01)00162-6

  日期：2001.9

  Bacterial chemotactic responses are initiated when certain small molecules (i.e., carbohydrates, amino acids) interact with bacterial chemoreceptors. Although bacterial chemotaxis has been the subject of intense investigations, few have explored the influence of attractant structure on signal generation and chemotaxis. Previously, we found that polymers bearing multiple copies of galactose interact with the chemoreceptor Trg via the periplasmic binding protein glucose/galactose binding protein (GGBP). These synthetic multivalent ligands were potent agonists of Escherichia coli chemotaxis. Here, we report on the development of a second generation of multivalent attractants that possess increased chemotactic activities. Strikingly, the new ligands can alter bacterial behavior at concentrations 10-fold lower than those required with the original displays; thus, they are some of the most potent synthetic chemoattractants known. The potency depends on the number of galactose moieties attached to the oligomer backbone and the length of the linker tethering these carbohydrates. Our investigations reveal the plasticity of GGBP; it can bind and mediate responses to several carbohydrates and carbohydrate derivatives. These attributes of GGBP may underlie the ability of bacteria to sense a variety of ligands with relatively few receptors. Our results provide insight into the design and development of compounds that can modulate bacterial chemotaxis and pathogenicity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin
  作者：Melanie Rauschenberg、Eva-Corrina Fritz、Christian Schulz、Tobias Kaufmann、Bart Jan Ravoo

  DOI：10.3762/bjoc.10.138

  日期：——

  two carbohydrates. The selectivity of the synthetic lectin was investigated by incubation on the immobilized carbohydrates. Selective binding of the synthetic lectin to immobilized NANA and beta-D-galactose was observed by fluorescence microscopy. The selectivity and affinity of the synthetic lectin was screened in competition experiments. In addition, the carbohydrate binding of the synthetic lectin

  碳水化合物和蛋白质的分子识别介导了广泛的生理过程，合成碳水化合物受体（“合成凝集素”）的发展构成了生物医学技术的关键进步。在这篇文章中，我们报告了一种合成凝集素，它选择性地与固定在分子单层中的碳水化合物结合。受我们之前工作的启发，我们制备了一种荧光标记的合成凝集素，由三肽 Cys-His-Cys 的环状二聚体组成，其通过单体的空气氧化自发形成。N-乙酰神经氨酸 (NANA)、β-D-半乳糖、β-D-葡萄糖和 α-D-甘露糖的胺系衍生物微接触印在环氧化物终止的自组装单层上。连续打印产生了两种碳水化合物的简单微阵列。通过在固定化碳水化合物上孵育来研究合成凝集素的选择性。通过荧光显微镜观察合成凝集素与固定化 NANA 和β-D-半乳糖的选择性结合。在竞争实验中筛选了合成凝集素的选择性和亲和力。此外，将合成凝集素的碳水化合物结合与凝集素伴刀豆球蛋白 A 和花生凝集素的碳水化合物结合进行了比较。发现