prenocardiamide B | 1431735-04-4

• 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: prenocardiamide B
• 英文别名: L-Tyr-L-Val-D-Leu-D-Val-L-Val-D-Val；Prenocardiamide B；(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-amino-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
• CAS: 1431735-04-4
• 化学式: C₃₅H₅₈N₆O₈
• 分子量: 690.881
• InChiKey: BMEQUJFAYBYIFH-IFZRAKSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  229
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  prenocardiamide B 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以10.7%的产率得到nocardiamide B
  参考文献：
  名称：

  Nocardiamides A and B, Two Cyclohexapeptides from the Marine-Derived Actinomycete Nocardiopsis sp. CNX037

  摘要：

  Two new cyclic hexapeptides, nocardiamides A (1) and B (2), were isolated from the culture broth of marine-derived actinomycete CNX037 strain that was identified as a Nocardiopsis species. The planar structures of nocardiamides A (1) and B (2) were assigned on the basis of ID and 2D NMR and HRESIMS spectroscopic analyses. Their absolute configurations were deduced by the advanced Marfey's method and chiral-phase HPLC analysis. The challenge of locating two D- and one L-valine residue in 1 and 2 was accomplished by total synthesis using solid-phase peptide synthetic methods. Both 1 and 2 showed negligible antimicrobial activities against seven indicator strains and exhibited no cytotoxicity against HCT-116.

  DOI：

  10.1021/np400009a
• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-O-叔丁基-L-酪氨酸 、 Fmoc-D-亮氨酸 、 Fmoc-D-缬氨酸 在 2-chlorotrityl chloride polystyrene resin 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 以47.8%的产率得到prenocardiamide B
  参考文献：
  名称：

  Nocardiamides A and B, Two Cyclohexapeptides from the Marine-Derived Actinomycete Nocardiopsis sp. CNX037

  摘要：

  Two new cyclic hexapeptides, nocardiamides A (1) and B (2), were isolated from the culture broth of marine-derived actinomycete CNX037 strain that was identified as a Nocardiopsis species. The planar structures of nocardiamides A (1) and B (2) were assigned on the basis of ID and 2D NMR and HRESIMS spectroscopic analyses. Their absolute configurations were deduced by the advanced Marfey's method and chiral-phase HPLC analysis. The challenge of locating two D- and one L-valine residue in 1 and 2 was accomplished by total synthesis using solid-phase peptide synthetic methods. Both 1 and 2 showed negligible antimicrobial activities against seven indicator strains and exhibited no cytotoxicity against HCT-116.

  DOI：

  10.1021/np400009a

文献信息

• Nocardiamides A and B, Two Cyclohexapeptides from the Marine-Derived Actinomycete <i>Nocardiopsis</i> sp. CNX037
  作者：Zheng-Chao Wu、Sumei Li、Sang-Jip Nam、Zhong Liu、Changsheng Zhang

  DOI：10.1021/np400009a

  日期：2013.4.26

  Two new cyclic hexapeptides, nocardiamides A (1) and B (2), were isolated from the culture broth of marine-derived actinomycete CNX037 strain that was identified as a Nocardiopsis species. The planar structures of nocardiamides A (1) and B (2) were assigned on the basis of ID and 2D NMR and HRESIMS spectroscopic analyses. Their absolute configurations were deduced by the advanced Marfey's method and chiral-phase HPLC analysis. The challenge of locating two D- and one L-valine residue in 1 and 2 was accomplished by total synthesis using solid-phase peptide synthetic methods. Both 1 and 2 showed negligible antimicrobial activities against seven indicator strains and exhibited no cytotoxicity against HCT-116.