padanamide A | 1314881-80-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: padanamide A
• 英文别名: (3S)-N-[(2S,3S,4S)-5-[[(3S)-1-carbamoyl-2-oxopyrrolidin-3-yl]amino]-3-hydroxy-4-methyl-5-oxo-1-phenylpentan-2-yl]-2-[(2R,3R)-3-hydroxy-2-[(2-methoxyacetyl)amino]-4-methylpentanoyl]diazinane-3-carboxamide
• CAS: 1314881-80-5
• 化学式: C₃₁H₄₇N₇O₉
• 分子量: 661.756
• InChiKey: IAYPOIKGUHHBAU-DYTCPEOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  233
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  padanamide A 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Isolation and characterization of actinoramides A–C, highly modified peptides from a marine Streptomyces sp.

  摘要：

  Reported herein is the isolation and structure elucidation of three highly modified peptides, actinoramides A-C (1-3), which are produced by a marine bacterium closely related to the genus Streptomyces. The planar structures of the actinoramides, which are composed of the unusual amino acids 2-amino-4-ureidobutanoic acid and 4-amino-3-hydroxy-2-methyl-5-phenylpentanoic acid, were assigned by chemical transformations and by interpretation of spectroscopic data, while the absolute configuration of these new peptides were defined by application of the advanced Marfey's and Mosher's methods. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.051
• 作为产物：
  描述：

  N-Cbz-L-苯丙氨醛 在 N-甲基吗啉 、 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 palladium 10% on activated carbon 、 C₉H₁₈BF₃O₂S 、 氢氟酸 、 水 、 氢气 、 双氧水 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 lithium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 45.5h， 生成 padanamide A
  参考文献：
  名称：

  Total synthesis of padanamides A and B

  摘要：

  首次完成了padanamides A和B的全合成，明确确认了它们的结构。

  DOI：

  10.1039/c3cc00178d

文献信息

• Actinoramide A Identified as a Potent Antimalarial from Titration-Based Screening of Marine Natural Product Extracts
  作者：Ken Chih-Chien Cheng、Shugeng Cao、Avi Raveh、Ryan MacArthur、Patricia Dranchak、George Chlipala、Matthew T. Okoneski、Rajarshi Guha、Richard T. Eastman、Jing Yuan、Pamela J. Schultz、Xin-zhuan Su、Giselle Tamayo-Castillo、Teatulohi Matainaho、Jon Clardy、David H. Sherman、James Inglese

  DOI：10.1021/acs.jnatprod.5b00489

  日期：2015.10.23

  Methods to identify the bioactive diversity within natural product extracts (NPEs) continue to evolve. NPEs constitute complex mixtures of chemical substances varying in structure, composition, and abundance. NPEs can therefore be challenging to evaluate efficiently with high-throughput screening approaches designed to test pure substances. Here we facilitate the rapid identification and prioritization of antimalarial NPEs using a pharmacologically driven, quantitative high-throughput-screening (qHTS) paradigm. In qHTS each NPE is tested across a concentration range from which sigmoidal response, efficacy, and apparent EC(50)s can be used to rank order NPEs for subsequent organism reculture, extraction, and fractionation. Using an NPE library derived from diverse marine microorganisms we observed potent antimalarial activity from two Streptomyces sp. extracts identified from thousands tested using qHTS. Seven compounds were isolated from two phylogenetically related Streptomyces species: Streptomyces ballenaensis collected from Costa Rica and Streptomyces bangulaensis collected from Papua New Guinea. Among them we identified actinoramides A and B, belonging to the unusually elaborated nonproteinogenic amino-acid-containing tetrapeptide series of natural products. In addition, we characterized a series of new compounds, including an artifact, 25-epi-actinoramide A, and actinoramides D, E, and F, which are closely related biosynthetic congeners of the previously reported metabolites.
• Total synthesis of padanamides A and B
  作者：Bohua Long、Shoubin Tang、Ligong Chen、Shiwei Qu、Bo Chen、Junyang Liu、Anita R. Maguire、Zhuo Wang、Yuqing Liu、Hui Zhang、Zhengshuang Xu、Tao Ye

  DOI：10.1039/c3cc00178d

  日期：——

  The first total syntheses of padanamides A and B have been achieved, unambiguously confirming their structures.

  首次完成了padanamides A和B的全合成，明确确认了它们的结构。
• Isolation and characterization of actinoramides A–C, highly modified peptides from a marine Streptomyces sp.
  作者：Sang-Jip Nam、Christopher A. Kauffman、Paul R. Jensen、William Fenical

  DOI：10.1016/j.tet.2011.04.051

  日期：2011.9

  Reported herein is the isolation and structure elucidation of three highly modified peptides, actinoramides A-C (1-3), which are produced by a marine bacterium closely related to the genus Streptomyces. The planar structures of the actinoramides, which are composed of the unusual amino acids 2-amino-4-ureidobutanoic acid and 4-amino-3-hydroxy-2-methyl-5-phenylpentanoic acid, were assigned by chemical transformations and by interpretation of spectroscopic data, while the absolute configuration of these new peptides were defined by application of the advanced Marfey's and Mosher's methods. (C) 2011 Elsevier Ltd. All rights reserved.