L-2-amino-5-phosphono-3-cis-pentenoic acid | 114376-26-0

• 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: L-2-amino-5-phosphono-3-cis-pentenoic acid
• 英文别名: L-APPA；(S,Z)-2-amino-5-phosphonopent-3-enoic acid；(z)-l-2-Amino-5-phosphono-3-pentenoic acid；(Z,2S)-2-amino-5-phosphonopent-3-enoic acid
• CAS: 114376-26-0
• 化学式: C₅H₁₀NO₅P
• 分子量: 195.112
• InChiKey: TUMOUMLCWZEIRK-XDSMRRFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 L-2-amino-5-phosphono-3-cis-pentenoic acid 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 以69%的产率得到
  参考文献：
  名称：

  Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizocticin A and Plumbemycin A

  摘要：

  Rhizocticins and Plumbemycins are natural phosphonate antibiotics produced by the bacterial strains Bacillus subtilis ATCC 6633 and Streptomyces plumbeus, respectively. Up to now, these potential threonine synthase inhibitors have only been synthesized under enzymatic catalysis. Here we report the chemical stereoselective synthesis of the non-proteinogenic (S,Z)-2-amino-5-phosphonopent-3-enoic acid [(S,Z)-APPA] and its use for the synthesis of Rhizocticin A and Plumbemycin A. In this work, (S,Z)-APPA was synthesized via the Still-Gennari olefination starting from Garner's aldehyde. The Michaelis-Arbuzov reaction was used to form the phosphorus-carbon bond. Oligopeptides were prepared using liquid phase peptide synthesis (LPPS) and were tested against selected bacteria and fungi. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.064
• 作为产物：
  描述：

  (S,Z)-tert-butyl 4-(3-bromoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate 在 chromium(VI) oxide 、 三甲基溴硅烷 、 水 、 potassium carbonate 、 高碘酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 25.5h， 生成 L-2-amino-5-phosphono-3-cis-pentenoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizocticin A and Plumbemycin A

  摘要：

  Rhizocticins and Plumbemycins are natural phosphonate antibiotics produced by the bacterial strains Bacillus subtilis ATCC 6633 and Streptomyces plumbeus, respectively. Up to now, these potential threonine synthase inhibitors have only been synthesized under enzymatic catalysis. Here we report the chemical stereoselective synthesis of the non-proteinogenic (S,Z)-2-amino-5-phosphonopent-3-enoic acid [(S,Z)-APPA] and its use for the synthesis of Rhizocticin A and Plumbemycin A. In this work, (S,Z)-APPA was synthesized via the Still-Gennari olefination starting from Garner's aldehyde. The Michaelis-Arbuzov reaction was used to form the phosphorus-carbon bond. Oligopeptides were prepared using liquid phase peptide synthesis (LPPS) and were tested against selected bacteria and fungi. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.064

文献信息

• Rapp, Claudius; Jung, Guenther; Kugler, Martin, Liebigs Annalen der Chemie, 1988, p. 655 - 662
  作者：Rapp, Claudius、Jung, Guenther、Kugler, Martin、Loeffler, Wolfgang

  DOI：——

  日期：——
• RAPP, CLAUDIUS;JUNG, GUNTHER;KUGLER, MARTIN;LOEFFIER, WOLFGANG, LIEBIGS ANN. CHEM.,(1988) N 7, 655-661
  作者：RAPP, CLAUDIUS、JUNG, GUNTHER、KUGLER, MARTIN、LOEFFIER, WOLFGANG

  DOI：——

  日期：——
• Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizocticin A and Plumbemycin A
  作者：Mathias Gahungu、Anthony Arguelles-Arias、Patrick Fickers、Astrid Zervosen、Bernard Joris、Christian Damblon、André Luxen

  DOI：10.1016/j.bmc.2013.06.064

  日期：2013.9

  Rhizocticins and Plumbemycins are natural phosphonate antibiotics produced by the bacterial strains Bacillus subtilis ATCC 6633 and Streptomyces plumbeus, respectively. Up to now, these potential threonine synthase inhibitors have only been synthesized under enzymatic catalysis. Here we report the chemical stereoselective synthesis of the non-proteinogenic (S,Z)-2-amino-5-phosphonopent-3-enoic acid [(S,Z)-APPA] and its use for the synthesis of Rhizocticin A and Plumbemycin A. In this work, (S,Z)-APPA was synthesized via the Still-Gennari olefination starting from Garner's aldehyde. The Michaelis-Arbuzov reaction was used to form the phosphorus-carbon bond. Oligopeptides were prepared using liquid phase peptide synthesis (LPPS) and were tested against selected bacteria and fungi. (C) 2013 Elsevier Ltd. All rights reserved.