1-amino-1-deoxy-β-D-galactose | 6318-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-amino-1-deoxy-β-D-galactose
• 英文别名: β-D-galactopyranosylamine；β-D-galactosylamine；Galactosylamin；D-galactosylamine；(2R,3R,4S,5R,6R)-2-Amino-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2R,3R,4S,5R,6R)-2-amino-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 6318-23-6
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: WCWOEQFAYSXBRK-FPRJBGLDSA-N

物化性质

• 熔点：
  128-133°C
• 沸点：
  416.4±45.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  116
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099
• 储存条件：
  -20°C，充氩

反应信息

• 作为反应物：
  描述：

  1-amino-1-deoxy-β-D-galactose 在 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 Nα-fluorenylmethoxycarbonyl-Nβ-β-D-galactopyranosyl-L-aspargine
  参考文献：
  名称：

  Fmoc-protected, glycosylated asparagines potentially useful as reagents in the solid-phase synthesis of N-glycopeptides

  摘要：

  I-Amino 1-deoxy derivatives of unprotected O-beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta-D-glucopyranose, 2-acetamido-2-deoxy-D-galactose, D-galactose, lactose, D-fucose, D-mannose, and 2-deoxy-D-arabino-hexose were prepared and acylated with N-fluorenylmethoxycarbonylaspartic acid alpha-tert-butyl ester. The anomeric configuration of the N-glycosyl bond (including that of the mannose derivative) in each of the purified compounds was shown to be beta. The probable stability of the N-glycosyl and glycosidic bonds during the conditions of solid-phase peptide synthesis was investigated by treatment of the glycosylated asparagine derivatives with different concentrations of trifluoroacetic acid. Based on their stability, we found that Fmoc-Asn(sugar)-OH derivatives are excellent candidates for automated synthesis of biologically active glycopeptides.

  DOI：

  10.1016/0008-6215(92)80080-k
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以39.5%的产率得到1-amino-1-deoxy-β-D-galactose
  参考文献：
  名称：

  半乳糖亚胺和-胺衍生物识别氨基酸的实验和计算研究：试图理解凝集素与碳水化合物的相互作用。

  摘要：

  基于半乳糖基-萘-亚胺的衍生物，1-（β- d-吡喃半乳糖基-1'-脱氧-1'-亚氨基甲基）-2-羟基萘（GNI），和基于半乳糖基-萘基胺的衍生物，1-利用荧光和吸收光谱法研究了具有ONO结合核心的（galactopyranosyl-1'-deoxy-1'-aminomethyl）-2-hydroxy萘（GNA）对天然氨基酸的识别，并推导了相应的缔合常数。形成的复合物。GNI / GNA之间形成的复合体氨基酸通过电喷雾电离质谱（ESI / MS）进行支持。通过使用密度泛函理论的计算研究对复合物的结构进行了优化，并计算了复合物的稳定能，以证实GNI / GNA与氨基酸之间的相互作用。发现该相互作用本质上主要是氢键。这些相互作用使人联想到凝集素-碳水化合物和糖苷酶底物中的相互作用。因此，存在于GNI中的碳水化合物部分对氨基酸的-COOH基团显示出高特异性，这可能与存在于碳水化合物和多肽之间的这种相互作用有关。

  DOI：

  10.1021/jo0700979

文献信息

• Synthesis and Affinity Evaluation of a Small Library of Bidentate Cholera Toxin Ligands: Towards Nonhydrolyzable Ganglioside Mimics
  作者：Pavel Cheshev、Laura Morelli、Marco Marchesi、Črtomir Podlipnik、Maria Bergström、Anna Bernardi

  DOI：10.1002/chem.200902469

  日期：2010.2.8

  further derivatization that can be used for conjugation with polyvalent aglycons. Their affinity towards cholera toxin was assessed by weak affinity chromatography, which allowed a systematic evaluation and selection of the best candidates. Affinity could be enhanced up to one or two orders of magnitude over the affinity of the individual pharmacophoric sugar residues.

  合成并测试了一个以半乳糖和唾液酸为药效学碳水化合物残基的GM1神经节苷脂的不可水解模拟物的小型文库。所有化合物都是使用高效反应（包括点击化学方案）和避免O-糖苷键的高效反应前体合成的。一些活性最高的分子还具有进一步衍生化的特征，可用于与多价糖苷配基结合。通过弱亲和色谱法评估了它们对霍乱毒素的亲和力，从而可以系统地评估和选择最佳候选物。与单个药效团糖残基的亲和力相比，亲和力可以提高一个或两个数量级。
• The effect of monosaccharides on self-assembly of benzenetricarboxamides
  作者：Jue Wang、Wenjing Qi、Guosong Chen

  DOI：10.1016/j.cclet.2018.12.014

  日期：2019.3

  Abstract The interaction between monosaccharides exhibits an important role in the assembly of monosaccharide-containing molecules. In this work, three common monosaccharides, glucose, galactose and mannose, are employed to investigate the effect of monosaccharide on the self-assembly of benzenetricarboxamide (BTA) core-containing molecules. In the presence of monosaccharides, three benzenetricarboxamide

  摘要单糖之间的相互作用在含单糖分子的组装中起着重要作用。在这项工作中，使用三种常见的单糖，葡萄糖，半乳糖和甘露糖，来研究单糖对含苯三甲酰胺（BTA）核心分子的自组装的影响。在单糖存在下，三种苯三甲酰胺衍生物会聚集成不同的有序结构。当在核心和单糖之间的这些分子中引入丙氨酸接头时，三种类型的单糖BTA的形态变为无序，同时其结构随着丙氨酸接头长度的增加而变得相似，表明单糖作用的消失。
• Bioreduction activated prodrugs of camptothecin: molecular design, synthesis, activation mechanism and hypoxia selective cytotoxicity
  作者：Zhouen Zhang、Kazuhito Tanabe、Hiroshi Hatta、Sei-ichi Nishimoto

  DOI：10.1039/b502813b

  日期：——

  Several water-soluble derivatives (CPT3, CPT3a–d) of camptothecin (CPT) were synthesized, among which CPT3 bearing an N,N′-dimethyl-1-aminoethylcarbamate side-chain was further conjugated with reductively eliminating structural units of indolequinone, 4-nitrobenzyl alcohol and 4-nitrofuryl alcohol to produce novel prodrugs of camptothecin (CPT4–6). All CPT derivatives were of lower cytotoxicity than their parent compound of CPT. In contrast, CPT4 and CPT6 showed higher hypoxia selectivity of cytotoxicity towards tumor cells than CPT. A mechanism by which a representative prodrug CPT4 is activated in the presence of DT-diaphorase to release CPT was also discussed. The bioreduction activated CPT prodrugs including CPT4 and CPT6 are identified to be promising for application to the hypoxia targeting tumor chemotherapy.

  合成了几种水溶性喜树碱衍生物(CPT3、CPT3a-d)，其中带有N,N′-二甲基-1-氨基乙基氨基甲酸酯侧链的CPT3进一步与吲哚醌、4-硝基苄醇和4-硝基糠醇的可还原消除结构单元偶联，产生了新的喜树碱前药(CPT4-6)。所有CPT衍生物的细胞毒性都低于其母体化合物CPT。相比之下，CPT4和CPT6对肿瘤细胞的缺氧选择性细胞毒性高于CPT。还讨论了一种代表性前药CPT4在存在DT-二氢酶的条件下释放CPT的激活机制。包括CPT4和CPT6在内的生物还原激活的CPT前药被认为有望应用于靶向缺氧肿瘤的化疗。
• Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids
  作者：Laiqiang Ying、Jacquelyn Gervay-Hague

  DOI：10.1016/j.carres.2003.10.018

  日期：2004.1

  The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis

  描述了适于固相合成的10种N-（氟-9-基甲氧基羰基）甘露糖基氨基糖醛酸的合成。一般的合成策略包括首先引入受保护的胺，然后对C-6羟基进行TEMPO选择性氧化，得到相应的Fmoc保护的糖氨基酸。胺的掺入可通过游离糖的氨解或糖基叠氮化物的还原来完成。该反应可以以多克级进行，从而提供了访问独特单体单元的途径，以便将来将其并入组合文库合成中。
• Discovery of potent inhibitor for farnesyl pyrophosphate synthase in the mevalonate pathway
  作者：Jinbo Gao、Xiusheng Chu、Yongge Qiu、Long Wu、Yuqin Qiao、Jiasheng Wu、Ding Li

  DOI：10.1039/c0cc00992j

  日期：——

  The mevalonate pathway is an important drug target for the treatment of cancer and cardiovascular disease. We synthesized and studied a new type of nitrogen-containing bisphosphonate analogs and developed a sensitive end point assay method for enzyme FPPS, which was used for inhibitor screening. One potent FPPS inhibitor was discovered, and the structure-activity relationship of bisphosphonates for

  甲羟戊酸途径是治疗癌症和心血管疾病的重要药物靶标。我们合成并研究了一种新型的含氮双膦酸盐类似物，并开发了用于酶FPPS的灵敏的终点测定方法，该方法用于抑制剂筛选。发现了一种有效的FPPS抑制剂，并研究了双膦酸酯对酶失活的构效关系。