benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactate | 153052-70-1

• 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: benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactate
• 英文别名: Boc-N(Me)Leu-D-OPhe-OBn；[(2R)-1-oxo-3-phenyl-1-phenylmethoxypropan-2-yl] (2S)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoate
• CAS: 153052-70-1
• 化学式: C₂₈H₃₇NO₆
• 分子量: 483.605
• InChiKey: AQPFGHHPZVNKFV-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl N-methyl-L-leucyl-3-phenyl-D-lactate
  参考文献：
  名称：

  Ohyama, Makoto; Iinuma, Katsuharu; Isogai, Akira, Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 6, p. 1193 - 1194

  摘要：

  DOI：
• 作为产物：
  描述：

  BOC-L-亮氨酸 在 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactate
  参考文献：
  名称：

  Ohyama, Makoto; Iinuma, Katsuharu; Isogai, Akira, Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 6, p. 1193 - 1194

  摘要：

  DOI：

文献信息

• Segment Solid-Phase Total Synthesis of the Anthelmintic Cyclooctadepsipeptides PF1022A and Emodepside
  作者：Jürgen Scherkenbeck、Sebastian Lüttenberg、Monika Ludwig、Karin Brücher、Andreas Kotthaus

  DOI：10.1002/ejoc.201101421

  日期：2012.3

  of N-methyl amino acids and hydroxycarboxylic acids. We report herein an efficient synthesis of the anthelmintic PF1022A and its commercial analogue emodepside on Kaiser and Wang resins. Our protocol provides the basis for the solid-phase synthesis of cyclodepsipeptide libraries with a high probability of anthelmintic, antibacterial or insecticidal activity.

  环缩肽、PF1022 和 verticilide 家族代表了多种多样的非常有趣的天然产物，因为它们具有多种生物活性。然而，到目前为止，还没有完成这些化合物的切实可行的固相合成，这可能是由于 N-甲基氨基酸和羟基羧酸的组合存在问题。我们在此报告了一种在 Kaiser 和 Wang 树脂上有效合成驱虫剂 PF1022A 及其商业模拟物艾莫德苷的方法。我们的协议为环缩肽库的固相合成提供了基础，具有很高的驱虫、抗菌或杀虫活性。
• Synthesis of PF1022A, an anthelmintic cyclodepsipeptide.
  作者：FRED E. BUTTON、STEPHEN J. NELSON

  DOI：10.7164/antibiotics.47.1322

  日期：——

  Anthelmintic cyclodepsipeptide PF1022A has been prepared in eleven steps from N-Boc-N-methyl-L-leucine, benzyl 3-phenyl-D-lactate and benzyl D-lactate.

  驱虫环肽PF1022A由N-Boc-N-甲基-L-亮氨酸、3-苯基-D-乳酸苄酯和D-乳酸苄酯通过11个步骤制备而成。
• Azadepsipeptides:  Synthesis and Evaluation of a Novel Class of Peptidomimetics
  作者：Hubert Dyker、Jürgen Scherkenbeck、Daniel Gondol、Axel Goehrt、Achim Harder

  DOI：10.1021/jo001749v

  日期：2001.6.1

  A general route to azadepsipeptides, a new class of pseudopeptides, has been established. The methodology was applied to the synthesis of a bis-aza analogue of the antiparasitic cyclooctadepsipeptide PF1022A. Comparison of the X-ray crystal structures of natural PF1022A (8) and the chimeric aza analogue 9 revealed that the introduction of nitrogen in the backbone of PF1022A results in almost complete conservation of the 3D structure with only minor deviations at the new nitrogen positions.
• Restricted Conformation Analogues of an Anthelmintic Cyclodepsipeptide
  作者：Fred E. Dutton、Byung H. Lee、Sandra S. Johnson、Eileen M. Coscarelli、Pil H. Lee

  DOI：10.1021/jm020482k

  日期：2003.5.1

  Six analogues of the anthelmintic cyclodepsipeptide PF1022A were prepared, each containing a small ring fused to the macrocycle to restrict the number of conformations the larger ring can adopt. It was anticipated that such conformational changes could lead to enhanced biological activity and selectivity. The analogues form two series of three members each. In one series, a carbon-based molecular bridge joins the methyl of a leucine residue with the methyl of its closest lactic acid residue to form five-, six-, and seven-membered lactam rings. In the second series, a leucine residue is replaced with five-, six-, and seven-membered nitrogen heterocycles. Decreasing the size of the small ring in the lactam. series increasingly distorts the macrocycle and consistently decreases activity relative to PF1022A. In the leucine series, a similar trend is observed. Molecular modeling of PF1022A along with the analogues described herein suggests that the ability to exist in a highly symmetrical conformational state is a necessary condition for biological activity.