钙吡内酰胺 | 1205538-83-5

• 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: 钙吡内酰胺
• 英文名称: Calpinactam
• 英文别名: (4R)-4-[[(2S)-2-[[(2S)-2-[[(2R)-2-amino-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-5-[[(2R,3S)-3-methyl-1-oxo-1-[[(3S)-2-oxoazepan-3-yl]amino]pentan-2-yl]amino]-5-oxopentanoic acid
• CAS: 1205538-83-5
• 化学式: C₃₈H₅₇N₉O₈
• 分子量: 767.926
• InChiKey: GPDRWULXOJRYOR-XHGFRBTRSA-N

物化性质

• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  55
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  267
• 氢给体数：
  9
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  calpinactam 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.0h， 以37%的产率得到钙吡内酰胺
  参考文献：
  名称：

  Synthesis and antimycobacterial activity of calpinactam derivatives

  摘要：

  Synthesis of calpinactam 1, a fungal antimycobacterial metabolite, utilizing solid-phase peptide synthesis is described. To explore the structure-activity relationships of 1, its derivatives with different amino acids were also synthesized on the basis of the same synthetic strategy. These derivatives were examined for antimycobacterial activity against Mycobacterium smegmatis. Among them, only peptide 6d having D-Ala in place of D-Glu showed moderate activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.069

文献信息

• Structure and Total Synthesis of Fungal Calpinactam, A New Antimycobacterial Agent
  作者：Nobuhiro Koyama、Shigenobu Kojima、Takeo Fukuda、Tohru Nagamitsu、Tadashi Yasuhara、Satoshi O̅mura、Hiroshi Tomoda

  DOI：10.1021/ol902553z

  日期：2010.2.5

  A new fungal metabolite designated calpinactam (1) was isolated from the culture broth of Mortierella alpina FKI-4905, and its structure was elucidated by spectroscopic analyses including NMR experiments. Calpinactam was found to be a hexapeptide with a caprolactam ring at its C-terminal. Its absolute stereochemistry was determined by amino acid analysis and total synthesis. Calpinactam selectively

  从高山被孢霉FKI-4905的培养液中分离出一种新的真菌代谢物，称为calpinactam（1），并通过包括NMR实验在内的光谱分析阐明了其结构。发现丙内酰胺是在其C-末端具有己内酰胺环的六肽。通过氨基酸分析和全合成确定其绝对立体化学。钙内酰胺选择性抑制分枝杆菌在各种微生物中的生长。钙吡内酰胺对耻垢分枝杆菌和结核分枝杆菌的MIC值分别为0.78和12.5μg/ mL。
• Development of a nitrogen-bound hydrophobic auxiliary: application to solid/hydrophobic-tag relay synthesis of calpinactam
  作者：Hiroki Nakahara、Goh Sennari、Yoshihiko Noguchi、Tomoyasu Hirose、Toshiaki Sunazuka

  DOI：10.1039/d3sc01432k

  日期：——

  In the last couple of decades, technologies and strategies for peptide synthesis have advanced rapidly. Although solid-phase peptide synthesis (SPPS) and liquid-phase peptide synthesis (LPPS) have contributed significantly to the development of the field, there have been remaining challenges for C-terminal modifications of peptide compounds in SPPS and LPPS. Orthogonal to the current standard approach

  在过去的几十年里，肽合成的技术和策略发展迅速。尽管固相肽合成（SPPS）和液相肽合成（LPPS）对该领域的发展做出了重大贡献，但SPPS和LPPS中肽化合物的C端修饰仍然存在挑战。与当前依赖于在氨基酸 C 末端安装载体分子的标准方法正交，我们开发了一种新的疏水性标签碳酸酯试剂，该试剂有助于稳健地制备氮标签支持的肽化合物。该助剂可轻松安装在各种氨基酸上，包括具有多种非规范残基的寡肽，从而可以通过结晶和过滤对产品进行简单纯化。我们展示了一个使用氮结合助剂进行 calpinactam 全合成的从头固体/疏水标签中继合成 (STRS) 策略。
• Synthesis and antimycobacterial activity of calpinactam derivatives
  作者：Kenichiro Nagai、Nobuhiro Koyama、Noriko Sato、Chisato Yanagisawa、Hiroshi Tomoda

  DOI：10.1016/j.bmcl.2012.09.069

  日期：2012.12

  Synthesis of calpinactam 1, a fungal antimycobacterial metabolite, utilizing solid-phase peptide synthesis is described. To explore the structure-activity relationships of 1, its derivatives with different amino acids were also synthesized on the basis of the same synthetic strategy. These derivatives were examined for antimycobacterial activity against Mycobacterium smegmatis. Among them, only peptide 6d having D-Ala in place of D-Glu showed moderate activity. (C) 2012 Elsevier Ltd. All rights reserved.