4-aminophenyl α-D-glucopyranoside | 31302-52-0

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-aminophenyl α-D-glucopyranoside
• 英文别名: 4-Aminophenyl-alpha-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-(4-aminophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 31302-52-0
• 化学式: C₁₂H₁₇NO₆
• 分子量: 271.27
• InChiKey: MIAKOEWBCMPCQR-ZIQFBCGOSA-N

物化性质

• 熔点：
  185-186℃
• 沸点：
  556℃
• 密度：
  1.517
• 闪点：
  290℃
• 溶解度：
  DMSO（轻微）、甲醇（轻微、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  对硝基苯-α-D-葡萄糖吡喃苷	4-nitrophenyl-α-D-glucopyranoside	3767-28-0	C12H15NO8	301.253

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	p-Acryloylaminophenyl α-D-glucopyranoside	——	C15H19NO7	325.318
  ——	4-(3,4-dinitrophenylamino)phenyl α-D-glucopyranoside	——	C18H19N3O10	437.363
  ——	4-(2,6-dinitrophenylamino)phenyl α-D-glucopyranoside	——	C18H19N3O10	437.363
  ——	4-(2,4-dinitrophenylamino)phenyl α-D-glucopyranoside	176757-24-7	C18H19N3O10	437.363
  ——	4-(2,4,6-trinitrophenylamino)phenyl α-D-glucopyranoside	——	C18H18N4O12	482.361
  ——	3β-cholest-5-en-3-yl N-[4-(α-D-glucopyranosyl)phenyl]carbamate	——	C40H61NO8	683.926

反应信息

• 作为反应物：
  描述：

  4-aminophenyl α-D-glucopyranoside 生成 4-oxo-4-[4-[(2R,3S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanilino]butanoic acid
  参考文献：
  名称：

  KIM, WAN, S.;JEONG, SEO, Y.;MCREA, J. C.

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯-α-D-葡萄糖吡喃苷 在 氢气 作用下， 生成 4-aminophenyl α-D-glucopyranoside
  参考文献：
  名称：

  方酸单酰胺甘露糖苷作为细菌凝集素FimH的配体：共价抑制还是没有？

  摘要：

  特定抗粘剂的候选人：方酸（SA）单酰胺具有非特异性地与胺交联的能力。已经显示，甘露聚糖SA单酰胺充当细菌凝集素FimH的特异性抑制剂，并且在凝集素的碳水化合物结合位点（CRD）内未发生共价生物缀合。

  DOI：

  10.1002/cbic.201000774

文献信息

• Sol–gel phase transition induced by fiber–vesicle structural changes in sugar-based bolaamphiphiles
  作者：Hideki Kobayashi、Kazuya Koumoto、Jong Hwa Jung、Seiji Shinkai

  DOI：10.1039/b204631h

  日期：——

  The research objects of this paper were to design bolaamphiphilic gelators utilizing a sugar family as a source of solvophilic groups and an azobenzene segment as a solvophobic group and to monitor the aggregation mode utilizing the spectroscopic properties of the azobenzene chromophore. The results indicated that the bolaamphiphiles act, although only for specific DMSO–water mixtures, as gelators and form a unique supramolecular helical structure in the gel phase. The UV-Vis and CD spectra showed that the azobenzene segments adopt H-type face-to-face orientation and the dipole moments are arranged in the right-handed (R)-helicity. Since the fibrils as observed by electron microscope possess the right-handed helical structure, one may consider that the microscopic azobenzene–azobenzene orientation is reflected by the macroscopic supramolecular structure. When boronic acid-appended poly(L-lysine) was added, the gel phase was changed into the sol phase in the macroscopic level and the fibrous aggregate was changed into the vesicular aggregate in the microscopic level. These changes, which are usually induced by a temperature change, are due to the specific boronic acid–sugar interaction occurring at the constant temperature. Interestingly, when D-fructose which shows high affinity with the boronic acid group was added, the sol phase and the vesicular aggregate were changed back to the gel phase and the fibrous aggregate, respectively. This means that the phase and morphological changes in the sugar-integrated bolaamphiphiles can be controlled reversibly.

  本文的研究对象是设计以糖类为溶亲基团来源、以偶氮苯片段为溶疏基团的双亲凝胶剂，并利用偶氮苯染料的光谱性质监测其聚集模式。研究结果表明，虽然双亲分子仅在特定的DMSO-水混合物中作为凝胶剂发挥作用，但它们在凝胶相中形成了独特的超分子螺旋结构。UV-Vis和圆二色光谱（CD）显示，偶氮苯片段呈现H型面对面取向，其偶极矩排列为右手性（R）螺旋。由于电子显微镜观察到的纤维具有右手螺旋结构，可以认为微观的偶氮苯-偶氮苯取向反映了宏观的超分子结构。当添加了具有羧基的聚（L-赖氨酸）时，凝胶相在宏观层面上转变为溶液相，细纤维聚集体在微观层面上转变为囊泡聚集体。这些变化通常是由温度变化引起的，但在恒定温度下由特定的羧酸-糖相互作用引起。值得注意的是，当添加与羧酸基团具有高亲和力的D-果糖时，溶液相和囊泡聚集体分别重新转变为凝胶相和细纤维聚集体。这意味着，糖整合的双亲分子的相和形态变化可以被可逆地控制。
• New Organogelators Bearing Both Sugar and Cholesterol Units: an Approach toward Molecular Design of Universal Gelators
  作者：Masato Amaike、Hideki Kobayashi、Seiji Shinkai

  DOI：10.1246/bcsj.73.2553

  日期：2000.11

  The gelators of organic solvents are classified into two categories on the basis of their basic intermolecular forces: hydrogen-bonded or nonhydrogen-bonded. To utilize these two interactions cooperatively for organogel formation we newly synthesized seven gelators (1—7) and two reference compounds (8 and 9) which have both a cholesterol moiety and a saccharide moiety within one molecule. The solubility

  有机溶剂的胶凝剂根据其基本分子间作用力分为两类：氢键或非氢键。为了协同利用这两种相互作用形成有机凝胶，我们新合成了七种凝胶剂 (1-7) 和两种参考化合物 (8 和 9)，它们在一个分子内同时具有胆固醇部分和糖类部分。根据糖的绝对构型，1-7 的溶解度从完全不溶到非常可溶。通常，当凝胶剂包含许多赤道 OH 基团时，它变得非常难溶，而当它包含许多轴向 OH 基团时，它变得非常易溶。带有两个赤道 OH 基团和一个轴向 OH 基团的凝胶剂 2 和 5 是良好的凝胶剂，在一些情况下，溶胶-凝胶相变温度（在密封管中测量）高于沸点。干凝胶的 SEM 观察结果表明，稳定的凝胶含有缠结的纤维网...
• Synthesis and Photochromic Properties of Configurationally Varied Azobenzene Glycosides
  作者：Vijayanand Chandrasekaran、Eugen Johannes、Hauke Kobarg、Frank D. Sönnichsen、Thisbe K. Lindhorst

  DOI：10.1002/open.201402010

  日期：2014.6

  glycoconjugates with favorable photochromic properties appear to be opportune. Here, a series of azobenzene glycosides were synthesized, employing glycoside synthesis and Mills reaction, to allow “switching” of carbohydrate orientation by reversible E/Z isomerization of the azobenzene N=N double bond. Their photochromic properties were tested and effects of azobenzene substitution as well as the effect

  碳水化合物的空间取向是碳水化合物识别过程中的一个有意义的参数。为了以时间和空间分辨率改变糖的方向，具有良好光致变色特性的光敏糖缀合物似乎是合适的。在这里，利用糖苷合成和米尔斯反应合成了一系列偶氮苯糖苷，通过偶氮苯 N=N 双键的可逆E / Z异构化来“转换”碳水化合物的取向。测试了它们的光致变色性能，并评估了偶氮苯取代的影响以及异头构型的影响和糖 2-羟基的取向。
• Modulating helicity through amphiphilicity—tuning supramolecular interactions for the controlled assembly of perylenes
  作者：Yongwei Huang、Jianchen Hu、Wenfeng Kuang、Zhixiang Wei、Charl F. J. Faul

  DOI：10.1039/c1cc10220f

  日期：——

  it is possible to modulate the supramolecular assembly of designed H-bonding amphiphilic perylene-based materials through simple solvent interactions. These modulated supramolecular interactions have been translated to and observed in macroscopic properties, and provide new pathways to the preparation of switchable interfaces based on designed supramolecular interactions.

  在这里，我们表明可以通过简单的溶剂相互作用来调节设计的H键两亲性per基材料的超分子组装。这些调节的超分子相互作用已被翻译成宏观性质并在宏观性质中观察到，并为基于设计的超分子相互作用而制备可切换界面提供了新途径。
• SYNTHETIC CATALYSTS FOR CARBOHYDRATE PROCESSING
  申请人：Iowa State University Research Foundation, Inc.

  公开号：US20220016612A1

  公开（公告）日：2022-01-20

  The disclosure relates to molecularly-imprinted cross-linked micelles that can selectively hydrolyze carbohydrates.

  该披露涉及分子印迹交联微胶束，可以选择性地水解碳水化合物。