N-methyl-((S)-azepan-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)dec-9-enamide | 1070777-03-5

• 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
• 英文名称: N-methyl-((S)-azepan-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)dec-9-enamide
• 英文别名: (12S,22S)-ciliatamide A；(S, S)-ciliatamide A；ciliatamide A；(S,S)-ciliatamide A；N-methyl-N-[(2S)-1-oxo-1-[[(3S)-2-oxoazepan-3-yl]amino]-3-phenylpropan-2-yl]dec-9-enamide
• CAS: 1070777-03-5
• 化学式: C₂₆H₃₉N₃O₃
• 分子量: 441.614
• InChiKey: UNVIKJZRLTXMOH-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  78.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-((S)-azepan-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)dec-9-enamide 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 L-N-Me-Phe-FDAA
  参考文献：
  名称：

  Isolation of Ciliatamide D from a Marine Sponge Stelletta sp. and a Reinvestigation of the Configuration of Ciliatamide A

  摘要：

  A new lipopeptide, ciliatamide D (1), was isolated from a marine sponge Stelletta sp., collected at Oshimashinsone, together with the known compound ciliatamide A (2). Ciliatamide D (1) is a congener of 2, in which N-Me-Phe is replaced by N-Me-Met(O). Marfey's analysis of the acid hydrolysate of 1 demonstrated that the two constituent amino acids were both in the L-form. This result prompted us to carefully investigate the configuration of 2, resulting in the assignment of the L-form for both residues.

  DOI：

  10.1021/np300878b
• 作为产物：
  描述：

  Boc-N-甲基-L-苯丙氨酸 在 2,4,6-三甲基吡啶 、 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 N-methyl-((S)-azepan-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)dec-9-enamide
  参考文献：
  名称：

  解决从海洋海绵的Ciliatamides，酰化的二肽的配置分配中的混乱。

  摘要：

  具有四个合成的异构体（正品ciliatamide A的直接比较1 - 4）通过NMR和手性相HPLC方法揭示ciliatamide A具有12 [R （d - ñ -MePhe残基）和22小号（升-Lys残基）的配置，这与我们之前的作业或其他人通过全面综合提出的作业都不相同。纤毛胺D中蛋氨酸亚砜残基的绝对构型也被修改为d。

  DOI：

  10.1021/acs.jnatprod.7b00684

文献信息

• Ring-closing metathesis based total synthesis of ciliatamides A and B and their structural confirmation
  作者：Krishnakumari Avula、Debendra K. Mohapatra

  DOI：10.1016/j.tetlet.2016.03.017

  日期：2016.4

  Protecting group dependant ring-closing metathesis based approach to the total synthesis of the revised structures of ciliatamides A and B has been described. The current synthetic strategy utilizes the amino acid as starting material to introduce both the stereogenic centers. However, usage of non-racemizing reagents (EDC·HCl, HATU/NMM); for amide coupling and Grubbs’ second generation catalyst for

  已经描述了基于保护基的基于闭环复分解的方法来完全合成纤毛酰胺A和B的修饰结构。当前的合成策略利用氨基酸作为起始材料来引入两个立体异构中心。但是，要使用非消旋试剂（EDC·HCl，HATU / NMM）；酰胺偶联的合成和格鲁布斯的第二代己内酰胺环合成催化剂使本方法更方便地获得关于绝对立体化学的正确结论。因此，基于与林德斯利报道的数据相似的旋光度值，该合成进一步支持纤毛酰胺A和B的实际立体化学为（R，R）。
• Total Synthesis of Ciliatamides A-C: Stereochemical Revision and the Natural Product-Guided Synthesis of Unnatural Analogs
  作者：Jana A. Lewis、R. Nathan Daniels、Craig W. Lindsley

  DOI：10.1021/ol801842v

  日期：2008.10.16

  The first total synthesis of Ciliatamides A-C was completed, leading to a revision of the reported stereochemistry from (SS) to the (R,R) enantiomers. Due to the expedited route, a library of over 50 unnatural ciliatamide analogs was also prepared.
• Isolation of Ciliatamide D from a Marine Sponge <i>Stelletta</i> sp. and a Reinvestigation of the Configuration of Ciliatamide A
  作者：Yasufumi Imae、Kentaro Takada、Shigeru Okada、Yuji Ise、Hiroshi Yoshimura、Yasuhiro Morii、Shigeki Matsunaga

  DOI：10.1021/np300878b

  日期：2013.4.26

  A new lipopeptide, ciliatamide D (1), was isolated from a marine sponge Stelletta sp., collected at Oshimashinsone, together with the known compound ciliatamide A (2). Ciliatamide D (1) is a congener of 2, in which N-Me-Phe is replaced by N-Me-Met(O). Marfey's analysis of the acid hydrolysate of 1 demonstrated that the two constituent amino acids were both in the L-form. This result prompted us to carefully investigate the configuration of 2, resulting in the assignment of the L-form for both residues.
• Resolution of the Confusion in the Assignments of Configuration for the Ciliatamides, Acylated Dipeptides from Marine Sponges
  作者：Kentaro Takada、Raku Irie、Rei Suo、Shigeki Matsunaga

  DOI：10.1021/acs.jnatprod.7b00684

  日期：2017.10.27

  revealed that ciliatamide A possesses the 12R (d-N-MePhe residue) and 22S (l-Lys residue) configurations, which were not identical with either our previous assignment or those proposed by others through total synthesis. The absolute configuration of the methionine sulfoxide residue in ciliatamide D was also revised to be d.

  具有四个合成的异构体（正品ciliatamide A的直接比较1 - 4）通过NMR和手性相HPLC方法揭示ciliatamide A具有12 [R （d - ñ -MePhe残基）和22小号（升-Lys残基）的配置，这与我们之前的作业或其他人通过全面综合提出的作业都不相同。纤毛胺D中蛋氨酸亚砜残基的绝对构型也被修改为d。