4-Amino-4-deoxy-D-erythronsaeure | 27294-73-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-Amino-4-deoxy-D-erythronsaeure
• 英文别名: (2R,3R)-4-Amino-2,3-dihydroxybutanoic acid
• CAS: 27294-73-1
• 化学式: C₄H₉NO₄
• 分子量: 135.12
• InChiKey: WITVYMTUWTVRND-PWNYCUMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Amino-4-deoxy-D-erythronsaeure 、 3',4',3,'',4'''-tetradehydro-3,2',6',2''',6'''-penta-Cbz-neomycin 在 N-羟基丁二酰亚胺 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Toxicity Modulation, Resistance Enzyme Evasion, and A-Site X-ray Structure of Broad-Spectrum Antibacterial Neomycin Analogs

  摘要：

  Aminoglycoside antibiotics are pseudosaccharides decorated with ammonium groups that are critical for their potent broad-spectrum antibacterial activity. Despite over three decades of speculation whether or not modulation of pK(a) is a viable strategy to curtail aminoglycoside kidney toxicity, there is a lack of methods to systematically probe amine-RNA interactions and resultant cytotoxicity trends. This study reports the first series of potent aminoglycoside antibiotics harboring fluorinated N1-hydroxyaminobutyryl acyl (HABA) appendages for which fluorine-RNA contacts are revealed through an X-ray cocrystal structure within the RNA A-site. Cytotoxicity in kidney-derived cells was significantly reduced for the derivative featuring our novel beta,beta-difluoro-HABA group, which masks one net charge by lowering the pK(a) without compromising antibacterial potency. This novel side-chain assists in evasion of aminoglycoside-modifying enzymes, and it can be easily transferred to impart these properties onto any number of novel analogs.

  DOI：

  10.1021/cb5003416
• 作为产物：
  描述：

  (2R,3R)-4-amino-4-deoxy-2,3-O-isopropylidene-D-erythronic acid 在 盐酸 作用下， 生成 4-Amino-4-deoxy-D-erythronsaeure
  参考文献：
  名称：

  Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima

  摘要：

  DOI：

  10.1021/ja00483a037

文献信息

• Toxicity Modulation, Resistance Enzyme Evasion, and A-Site X-ray Structure of Broad-Spectrum Antibacterial Neomycin Analogs
  作者：Juan Pablo Maianti、Hiroki Kanazawa、Paola Dozzo、Rowena D. Matias、Lee Ann Feeney、Eliana S. Armstrong、Darin J. Hildebrandt、Timothy R. Kane、Micah J. Gliedt、Adam A. Goldblum、Martin S. Linsell、James B. Aggen、Jiro Kondo、Stephen Hanessian

  DOI：10.1021/cb5003416

  日期：2014.9.19

  Aminoglycoside antibiotics are pseudosaccharides decorated with ammonium groups that are critical for their potent broad-spectrum antibacterial activity. Despite over three decades of speculation whether or not modulation of pK(a) is a viable strategy to curtail aminoglycoside kidney toxicity, there is a lack of methods to systematically probe amine-RNA interactions and resultant cytotoxicity trends. This study reports the first series of potent aminoglycoside antibiotics harboring fluorinated N1-hydroxyaminobutyryl acyl (HABA) appendages for which fluorine-RNA contacts are revealed through an X-ray cocrystal structure within the RNA A-site. Cytotoxicity in kidney-derived cells was significantly reduced for the derivative featuring our novel beta,beta-difluoro-HABA group, which masks one net charge by lowering the pK(a) without compromising antibacterial potency. This novel side-chain assists in evasion of aminoglycoside-modifying enzymes, and it can be easily transferred to impart these properties onto any number of novel analogs.
• Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima
  作者：James A. Musich、Henry Rapoport

  DOI：10.1021/ja00483a037

  日期：1978.7