Fmoc-L-Orn(pNZ)-OH | 870102-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-L-Orn(pNZ)-OH
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(4-nitrophenyl)methoxycarbonylamino]pentanoic acid
• CAS: 870102-82-2
• 化学式: C₂₈H₂₇N₃O₈
• 分子量: 533.538
• InChiKey: GAQVDOIBVGQYKV-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  160
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Fmoc-L-Orn(pNZ)-OH 、 Fmoc-L-丙氨酸 、 Fmoc-L-苯丙氨酸 生成 H-Orn(Phe)-Ala-NH₂
  参考文献：
  名称：

  Semipermanent p-nitrobenzyloxycarbonyl (pNZ) protection of Orn and Lys side chains: prevention of undesired α-Fmoc removal and application to the synthesis of cyclic peptides

  摘要：

  Semipermanent side-chain protection of Orn and Lys with p-nitrobenzyloxycarbonyl (pNZ) for Fmoc/'Bu chemistry does not result in the unwanted removal of alpha-Fmoc that occurs when groups such as Alloc are used for the same application. Furthermore, pNZ can be used in conjuction with p-nitrobenzyl ester (pNB) to prepare cyclic peptides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.043
• 作为产物：
  描述：

  N-Fmoc-N'-Boc-L-鸟氨酸 在 sodium azide 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 Fmoc-L-Orn(pNZ)-OH
  参考文献：
  名称：

  Use of p-nitrobenzyloxycarbonyl (pNZ) as a permanent protecting group in the synthesis of Kahalalide F analogs

  摘要：

  p-Nitrobenzyloxycarbonyl (pNZ) is used for the permanent protection of ornithine in the synthesis of derivatives of the anti-tumor cyclodepsipeptide Kahalalide F that contain acid labile residues. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.044

文献信息

• Semipermanent p-nitrobenzyloxycarbonyl (pNZ) protection of Orn and Lys side chains: prevention of undesired α-Fmoc removal and application to the synthesis of cyclic peptides
  作者：Albert Isidro-Llobet、Mercedes Álvarez、Fernando Albericio

  DOI：10.1016/j.tetlet.2005.09.043

  日期：2005.11

  Semipermanent side-chain protection of Orn and Lys with p-nitrobenzyloxycarbonyl (pNZ) for Fmoc/'Bu chemistry does not result in the unwanted removal of alpha-Fmoc that occurs when groups such as Alloc are used for the same application. Furthermore, pNZ can be used in conjuction with p-nitrobenzyl ester (pNB) to prepare cyclic peptides. (c) 2005 Elsevier Ltd. All rights reserved.
• Use of p-nitrobenzyloxycarbonyl (pNZ) as a permanent protecting group in the synthesis of Kahalalide F analogs
  作者：Pilar E. López、Albert Isidro-Llobet、Carolina Gracia、Luis J. Cruz、Andrés García-Granados、Andrés Parra、Mercedes Álvarez、Fernando Albericio

  DOI：10.1016/j.tetlet.2005.09.044

  日期：2005.11

  p-Nitrobenzyloxycarbonyl (pNZ) is used for the permanent protection of ornithine in the synthesis of derivatives of the anti-tumor cyclodepsipeptide Kahalalide F that contain acid labile residues. (c) 2005 Elsevier Ltd. All rights reserved.