((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid vinyl ester | 791064-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid vinyl ester
• CAS: 791064-19-2
• 化学式: C₁₅H₁₉NO₇
• 分子量: 325.318
• InChiKey: BCHYXLGJKQZELT-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  117.48
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid vinyl ester 在 Candida antarctica lipase B 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 96.0h， 生成 {3-[4-(3-Amino-propylamino)-butylamino]-propyl}-carbamic acid (2R,3S,4R,5R,6S)-5-(3-{3-[4-(3-amino-propylamino)-butylamino]-propyl}-ureido)-3,4-dihydroxy-6-phenoxy-tetrahydro-pyran-2-ylmethyl 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：

  氯甲酸乙烯酯 、 Phenyl-2-amino-2-deoxy-β-D-glucopyranosid 在 sodium hydroxide 作用下， 以 phosphate buffer 为溶剂， 反应 5.0h， 以67%的产率得到((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid 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