Phenyl-2-amino-2-deoxy-β-D-glucopyranosid | 38223-13-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phenyl-2-amino-2-deoxy-β-D-glucopyranosid
• 英文别名: (2R,3S,4R,5R,6S)-5-amino-2-(hydroxymethyl)-6-phenoxyoxane-3,4-diol
• CAS: 38223-13-1
• 化学式: C₁₂H₁₇NO₅
• 分子量: 255.271
• InChiKey: SZCRBYJIVDDZLQ-LZQZFOIKSA-N

物化性质

• 熔点：
  174-175 °C
• 沸点：
  481.0±45.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 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：
  105
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Phenyl-2-amino-2-deoxy-β-D-glucopyranosid 在 Candida antarctica lipase B 、 sodium hydroxide 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 5.0h， 生成 Carbonic acid (2R,3S,4R,5R,6S)-3,4-dihydroxy-6-phenoxy-5-vinyloxycarbonylamino-tetrahydro-pyran-2-ylmethyl ester vinyl ester
  参考文献：
  名称：

  Chemoenzymatic Synthesis and High-Throughput Screening of an Aminoglycoside−Polyamine Library:  Identification of High-Affinity Displacers and DNA-Binding Ligands

  摘要：

  Chemoenzymatic parallel synthesis and high-throughput screening were employed to develop a multivalent aminoglycoside-polyamine library for use as high-affinity cation-exchange displacers and DNA-binding ligands. Regioselective lipase-catalyzed acylation, followed by chemical aminolysis, was used to generate vinyl carbonate and vinyl carbamate linkers, respectively, of the aminoglycosidic cores. These were further derivatized with polyamines, leading to library generation. A parallel batch-displacement assay was employed to identify the efficacy of the library candidates as potential displacers for protein purification. Using this approach, low-molecular-mass displacers with affinities higher than those previously observed have been identified. The aminoglycoside-polyamine library was also screened for DNA binding efficacy using an ethidium bromide displacement assay. These highly cationic molecules exhibited strong DNA-binding properties and may have potential for enhanced gene delivery.

  DOI：

  10.1021/ja049437n
• 作为产物：
  描述：

  phenyl-3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalamido-β-D-glucopyranoside 在 乙二胺 作用下， 以 乙腈 为溶剂， 生成 Phenyl-2-amino-2-deoxy-β-D-glucopyranosid
  参考文献：
  名称：

  基于氨基葡萄糖的异氰酸酯的设计，合成和防污活性。

  摘要：

  生物污染是生物在海底结构（如船体和渔网）上的不良堆积，是一个严重的经济问题，其影响包括石油浪费和网眼堵塞。自1960年代以来，有机锡化合物一直被用作防污材料。但是，由于此类化合物对海洋生物具有高毒性，导致男性化和强加性，后来国际海事组织（IMO）禁止使用此类化合物。自禁令以来，人们一直在努力开发对环境无害的防污剂。从海洋生物获得的天然防污产品由于其强大的防污活性和低毒性而受到了广泛的关注。这些防污化合物通常含有异氰酸酯基，众所周知，它们具有天然的防污性能。基于我们之前对天然异氰酸类萜类化合物的全面合成，我们设想将异氰基官能团安装在葡糖胺上，以生产环保型防污材料。本文描述了一种有效的合成方法，用于各种基于氨基葡萄糖的异氰酸酯，并评估了它们对藤壶amphibalant amphitrite的塞浦路斯幼虫的防污活性和毒性。在端基位置具有醚官能团的氨基葡萄糖异氰酸酯具有很强的防污活性，EC50值低于1μg/

  DOI：

  10.3390/md15070203

文献信息

• Helferich et al., Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1934, vol. 226, p. 258,261
  作者：Helferich et al.

  DOI：——

  日期：——
• Design, Synthesis, and Antifouling Activity of Glucosamine-Based Isocyanides
  作者：Taiki Umezawa、Yuki Hasegawa、Ira Novita、Junya Suzuki、Tatsuya Morozumi、Yasuyuki Nogata、Erina Yoshimura、Fuyuhiko Matsuda

  DOI：10.3390/md15070203

  日期：——

  against cypris larvae of the barnacle Amphibalanus amphitrite. Glucosamine isocyanides with an ether functionality at the anomeric position exhibited potent antifouling activity, with EC50 values below 1 μg/mL, without detectable toxicity even at a high concentration of 10 μg/mL. Two isocyanides had EC50 values of 0.23 and 0.25 μg/mL, comparable to that of CuSO₄, which is used as a fouling inhibitor (EC50

  生物污染是生物在海底结构（如船体和渔网）上的不良堆积，是一个严重的经济问题，其影响包括石油浪费和网眼堵塞。自1960年代以来，有机锡化合物一直被用作防污材料。但是，由于此类化合物对海洋生物具有高毒性，导致男性化和强加性，后来国际海事组织（IMO）禁止使用此类化合物。自禁令以来，人们一直在努力开发对环境无害的防污剂。从海洋生物获得的天然防污产品由于其强大的防污活性和低毒性而受到了广泛的关注。这些防污化合物通常含有异氰酸酯基，众所周知，它们具有天然的防污性能。基于我们之前对天然异氰酸类萜类化合物的全面合成，我们设想将异氰基官能团安装在葡糖胺上，以生产环保型防污材料。本文描述了一种有效的合成方法，用于各种基于氨基葡萄糖的异氰酸酯，并评估了它们对藤壶amphibalant amphitrite的塞浦路斯幼虫的防污活性和毒性。在端基位置具有醚官能团的氨基葡萄糖异氰酸酯具有很强的防污活性，EC50值低于1μg/
• Chemoenzymatic Synthesis and High-Throughput Screening of an Aminoglycoside−Polyamine Library:  Identification of High-Affinity Displacers and DNA-Binding Ligands
  作者：Kaushal Rege、Shanghui Hu、James A. Moore、Jonathan S. Dordick、Steven M. Cramer

  DOI：10.1021/ja049437n

  日期：2004.10.1

  Chemoenzymatic parallel synthesis and high-throughput screening were employed to develop a multivalent aminoglycoside-polyamine library for use as high-affinity cation-exchange displacers and DNA-binding ligands. Regioselective lipase-catalyzed acylation, followed by chemical aminolysis, was used to generate vinyl carbonate and vinyl carbamate linkers, respectively, of the aminoglycosidic cores. These were further derivatized with polyamines, leading to library generation. A parallel batch-displacement assay was employed to identify the efficacy of the library candidates as potential displacers for protein purification. Using this approach, low-molecular-mass displacers with affinities higher than those previously observed have been identified. The aminoglycoside-polyamine library was also screened for DNA binding efficacy using an ethidium bromide displacement assay. These highly cationic molecules exhibited strong DNA-binding properties and may have potential for enhanced gene delivery.