丝核菌素A | 114301-25-6

• 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
• 中文名称: 丝核菌素A
• 英文名称: L-arginyl-5-phosphono-L-cis-3,4-didehydronorvaline
• 英文别名: Rhizocticin A；L-arginyl-2-amino-5-phosphono-3-cis-pentenoate；(Z,2S)-2-[[(2S)-2-azaniumyl-5-(diaminomethylideneazaniumyl)pentanoyl]amino]-5-[hydroxy(oxido)phosphoryl]pent-3-enoate
• CAS: 114301-25-6
• 化学式: C₁₁H₂₂N₅O₆P
• 分子量: 351.299
• InChiKey: BLNRPHBKOMCMBX-ABXVWLFBSA-N

物化性质

• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  丝核菌素A 在 N-ethylmorpholinium acetate 、 calcium chloride 作用下， 反应 30.0h， 生成 L-2-amino-5-phosphono-3-cis-pentenoic acid
  参考文献：
  名称：

  Rapp, Claudius; Jung, Guenther; Kugler, Martin, Liebigs Annalen der Chemie, 1988, p. 655 - 662

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-1,1-dimethylethyl 4-<(Z)-3'-methoxy-3'-oxo-1'-propenyl>-2,2-dimethyl-3-oxazolidinecarboxylate 在 chromium(VI) oxide 、 三甲基溴硅烷 、 四溴化碳 、 水 、 二异丁基氢化铝 、 potassium carbonate 、 potassium hydrogencarbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 高碘酸 、 三苯基膦 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 47.33h， 生成 丝核菌素A
  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, 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.
• 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：——