3-aminopropyl β-D-galactopyranoside | 201667-53-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-aminopropyl β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(3-aminopropoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；3-Aminopropyl beta-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-(3-aminopropoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 201667-53-0
• 化学式: C₉H₁₉NO₆
• 分子量: 237.253
• InChiKey: ATNZYMLQVJTLPA-QMGXLNLGSA-N

物化性质

• 沸点：
  480.0±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-aminopropyl β-D-galactopyranoside 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 3’-(N-methyl-N,N-di-n-dodecylammonium iodide)propylβ-D-galactopyranoside
  参考文献：
  名称：

  半乳糖衍生物阳离子脂质体纳米颗粒的制备 方法

  摘要：

  本发明公开了半乳糖衍生物阳离子脂质体纳米颗粒的制备方法。以半乳糖为原料，经全乙酰化、脱1‑O‑乙酰基、三氯乙酰亚胺酯化、糖苷化、叠氮化、脱全部乙酰基反应得中间体，再分别通过3,4‑O‑异丙叉基化、醚化、脱叉基、还原胺化、季铵盐化和还原氨化、叔胺化、季铵盐化反应，合成了两个系列不同物理结构的半乳糖衍生物阳离子脂质体；经水分散后得到相应阳离子脂质体纳米颗，其具有稳定性好、粒径及表面电荷适中、制备成本低等优点，能满足核酸药物转运载体应具备的基本要求。

  公开号：

  CN106267224B
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 sodium methylate 、 乙酸肼 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -30.0~60.0 ℃ 、344.74 kPa 条件下， 反应 22.0h， 生成 3-aminopropyl β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and Enzyme-Specific Activation of Carbohydrate−Geldanamycin Conjugates with Potent Anticancer Activity

  摘要：

  Geldanamycin (GA) is a potent anticancer antibiotic that inhibits Hsp90. Its potential clinical utility is hampered by its severe toxicity. To alleviate this problem, we synthesized a series of carbohydrate - geldanamycin conjugates for enzyine-specific activation to increase tumor selectivity. The conjugation was carried out at the C-17-position of GA. Their anticancer activity was tested in a number of cancer cell lines. The enzyme-specific activation of these conjugates M ion was evaluated with beta-galactosidase and beta-glucosidase. Evidently. glycosylation of C-17-pasition converted GA to an inactive prodrug before enzyme cleavage. Glucose-GA, as positive control, showed anticancer activity with IC50 of 70.2- 380.9 nM in various cancer cells by beta-glucocsidase activation inside of the tumor cells, which was confirmed by 3-fold inhibition using beta-glucasidase. specific inhibitor [2,5-dihydroxyniethy-3,4-dihydroxypyrrolidine (DMDP)]. Compared to glucose- GA, galactose- and lactose-GA conjugates exhibited much less activity with IC50 greater than 8000-25 000 nM. However, when galactose- and lactose-GA, were incubated with beta-galactosidase in the cells, their anticancer activity was enhanced by 3- to 40-fold. The results suggest, that GA can be inactivated by glycosylation of C-17-position and reactivated for anticancer activity by beta-galactosidase. Therefore, galactose-GA can be exploited in antibody-directed enzyme prodrug therapy (ADEPT) with beta-galactosidase for enzyme-specific activation in tumors. to increase tumor selectivity.

  DOI：

  10.1021/jm049693a

文献信息

• Monosaccharide Analogues of Anticancer Peptide R-Lycosin-I: Role of Monosaccharide Conjugation in Complexation and the Potential of Lung Cancer Targeting and Therapy
  作者：Peng Zhang、Jing Ma、Qianqian Zhang、Shandong Jian、Xiaoliang Sun、Bobo Liu、Liqin Nie、Meiyan Liu、Songping Liang、Youlin Zeng、Zhonghua Liu

  DOI：10.1021/acs.jmedchem.9b00634

  日期：2019.9.12

  promising modification strategy for the optimization of peptide drugs. In this study, five different monosaccharide derivatives (7a-e) were covalently linked to the N-terminal of R-lycosin-I, which yielded five glycopeptides (8a-e). They demonstrated increased or reduced cytotoxicity depending on monosaccharide types, which might be explained by the changes of physicochemical properties. Among all synthesized

  糖缀合是用于肽药物优化的有希望的修饰策略。在这项研究中，五个不同的单糖衍生物（7a-e）与R-lycosin-I的N端共价连接，产生了五个糖肽（8a-e）。他们显示出取决于单糖类型的细胞毒性增加或减少，这可以用理化性质的变化来解释。在所有合成的糖肽中，只有8a表现出增加的细胞毒性（IC50 = 9.6±0.3μM）和选择性（IC50 = 37.4±5.9μM）。癌细胞中高表达的葡萄糖转运蛋白1（GLUT1）被批准参与8a的细胞毒性和选择性增强。此外，在裸鼠异种移植模型中，8a抑制R-lycosin-I抑制肿瘤生长，而不会在腹膜内产生副作用。
• High-Avidity, Low-Affinity Multivalent Interactions and the Block to Polyspermy in <i>Xenopus </i><i>l</i><i>aevis</i>
  作者：Esther Arranz-Plaza、Alex S. Tracy、Aloysius Siriwardena、J. Michael Pierce、Geert-Jan Boons

  DOI：10.1021/ja020536f

  日期：2002.11.1

  derivatives by acetylation of the amino group or the synthesis of polyvalent compounds by attachment to an activated polyacrylamide polymer. A number of analytical techniques, including enzyme-linked lectin assays and surface plasmon resonance, have been developed and utilized to study the interactions of the mono- and polyvalent compounds with XL35. The results reveal that the lectin XL35 has remarkably

  凝集素 XL35 与爪蟾卵母细胞周围的果冻外壳蛋白 (JCP) 的相互作用对于阻止多精子症至关重要。这一事件的分子细节知之甚少，本研究旨在描绘受精包膜的形成机制。合成了一系列 JCP 衍生的低聚糖，并且都安装了人工氨基丙基臂。该臂允许通过氨基的乙酰化制备一价衍生物或通过连接到活化的聚丙烯酰胺聚合物来合成多价化合物。许多分析技术，包括酶联凝集素测定和表面等离子体共振，已被开发并用于研究单价和多价化合物与 XL35 的相互作用。结果表明，凝集素 XL35 对含半乳糖的糖类具有非常广泛的特异性，并且亲和力仅受次要特征的轻微调节，例如末端糖的异头构型或分支糖的身份和连接模式。当糖以多价方式存在时，也观察到广泛的特异性。与相应的单价对应物相比，糖聚合物的价校正亲和力增加了 10-20 倍。尽管合成聚合物不如 JCP 有效，但它们的相互作用动力学与天然配体的动力学非常相似，并且在每种情况下都观察到了极长的相互作用。这项研究的结果表明，在
• Synthesis of Galactoclusters by Metal-Free Thiol “Click Chemistry” and Their Binding Affinities for<i>Pseudomonas aeruginosa</i>Lectin LecA
  作者：Caroline Ligeour、Lucie Dupin、Alberto Marra、Gérard Vergoten、Albert Meyer、Alessandro Dondoni、Eliane Souteyrand、Jean-Jacques Vasseur、Yann Chevolot、François Morvan

  DOI：10.1002/ejoc.201402902

  日期：2014.12

  DNA-based glycoarray and compared with that of a galactocluster synthesised by copper-catalyzed azide–alkyne cycloaddition. The results indicated stronger binding of all galactoclusters relative to the monovalent galactoside but slightly weaker binding than that shown by the galactocluster incorporating a triazole ring, due to a favourable interaction of the latter with proline 51 of LecA.

  通过亚磷酰胺化学和无金属硫醇点击化学（即硫醇加成到丙烯酰胺或溴乙酰胺基团中的溴通过硫醇官能团进行亲核置换）的组合，合成了对铜绿假单胞菌凝集素 I 具有特异性的甘露糖中心半乳糖簇（LecA） . 这些硫醇点击反应是在 Et3N 存在下在微波辅助下进行的，并使用还原剂来避免二硫化物的形成。用 DNA 标签合成了九个含有不同接头（脂肪族、低聚乙二醇或芳香族）的四价半乳糖簇。它们与 LecA 的结合在基于 DNA 的糖阵列中进行监测，并与铜催化叠氮化物-炔烃环加成合成的半乳糖簇进行比较。
• Synthesis and Supramolecular Characterization of a Novel Class of Glycopyranosyl-Containing Amphiphiles
  作者：Frank Reichel、Annie M. Roelofsen、Hubertus P. M. Geurts、Sjerry J. van der Gaast、Martinus C. Feiters、Geert-Jan Boons

  DOI：10.1021/jo991685s

  日期：2000.6.1

  A novel class of glycopeptidolipids is described, which potentially can be used as a novel antigen-delivery system. The compounds have been prepared by a combination of solid-supported and solution-based methods. The use of the orthogonally protected FmocLysDde derivative provided an opportunity to incorporate two different types lipids. It was found that the model compound 1 forms aggregates in aqueous media which can be described as rod or tubelike structures. The aggregates can be stabilized by topotactic photopolymerization. Studies on the structural analogues 2-5 revealed the effect of the carbohydrate, peptide, and lipid moiety on the aggregation properties. It is concluded that none of the structure elements can lay claim to be exclusively important for the formation of highly organized aggregates such as tubes, fibers, or helical ribbons from 1, but the presence of all of these structural elements afforded the most uniformly shaped extended structures.
• Enzymatic synthesis of 3-aminopropyl-1-<i>O</i>-β-<scp>D</scp>-galactopyranoside catalyzed by<i>Aspergillus oryzae</i>β-galactosidase
  作者：Cecilia Porciúncula González、Ernesto Rodríguez、Silvia Soule、Laura Franco Fraguas、Beatriz M. Brena、Cecilia Giacomini、Gabriela Irazoqui

  DOI：10.3109/10242422.2015.1095678

  日期：2015.7.4

  Glycosidases represent excellent green chemistry alternatives as catalysts for the synthesis of glycosides, and in particular their stereoselectivity allows the production of anomerically pure glycosides, in only one reaction step using mild reaction conditions. Here, we report the enzymatic synthesis and structural characterization of 3-aminopropyl-1-O--D-galactopyranoside. Optimal reaction conditions for the transgalactosylation reaction were 100mM lactose, 500mM 3-amino-1-propanol and 24 h of incubation at 50 degrees C with 6 U/mL of -galactosidase from Aspergillus oryzae. The fact that the synthesis of 1-propyl-2-O--D-galactopyranoside using 1-amino-2-propanol as acceptor was not achieved, and that N-glycoside formation was not observed, confirms the selectivity of -galactosidase for the synthesis of O-glycosides, and particularly for primary alcohols. The synthesized galactosides were evaluated for their ability to interact with bovine spleen galectin-1 (Gal-1) by using the hemagglutination inhibition assay; results demonstrated that 3-aminopropyl-1-O--D-galactopyranoside may be considered as a functionalized galactose moiety more than an efficient Gal-1 inhibitor. The proposed approach constitutes a promising tool for the generation of glycopolymers and glyconanoparticles with potential applications in the development of biosensors as well as construction blocks in chemical synthesis.