(5-(((R)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-D-alanine | 194737-02-5

• 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: (5-(((R)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-D-alanine
• 英文别名: D-alanine-D-FDAA
• CAS: 194737-02-5
• 化学式: C₁₂H₁₅N₅O₇
• 分子量: 341.28
• InChiKey: QMGXWWJTXPWIMG-PHDIDXHHSA-N

物化性质

• 沸点：
  716.0±60.0 °C(Predicted)
• 密度：
  1.593±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  190.73
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  D-丙氨酸 、 D-FDAA 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 (5-(((R)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-D-alanine
  参考文献：
  名称：

  Lipopeptides from the Tropical Marine Cyanobacterium Symploca sp.

  摘要：

  A collection of the tropical marine cyanobacterium Symploca sp., collected near Kimbe Bay, Papua New Guinea, previously yielded several new metabolites including kimbeamides A-C, kimbelactone A, and tasihalide C. Investigations into a more polar cytotoxic fraction yielded three new lipopeptides, tasiamides C-E (1-3). The planar structures were deduced by 2D NMR spectroscopy and tandem mass spectrometry, and their absolute configurations were determined by a combination of Marfey's and chiral-phase GC-MS analysis. These new metabolites are similar to several previously isolated compounds, including tasiamide (4), grassystatins (5, 6), and symplocin A, all of which were isolated from similar filamentous marine cyanobacteria.

  DOI：

  10.1021/np401051z

文献信息

• Pagoamide A, a Cyclic Depsipeptide Isolated from a Cultured Marine Chlorophyte, <i>Derbesia</i> sp., Using MS/MS-Based Molecular Networking
  作者：Yueying Li、Hao-Bing Yu、Yi Zhang、Tiago Leao、Evgenia Glukhov、Marsha L. Pierce、Chen Zhang、Hyunwoo Kim、Huanru Henry Mao、Fang Fang、Garrison W. Cottrell、Thomas F. Murray、Lena Gerwick、Huashi Guan、William H. Gerwick

  DOI：10.1021/acs.jnatprod.9b01019

  日期：2020.3.27

  A thiazole-containing cyclic depsipeptide with 11 amino acid residues, named pagoamide A (1), was isolated from laboratory cultures of a marine Chlorophyte, Derbesia sp. This green algal sample was collected from America Samoa, and pagoamide A was isolated using guidance by MS/MS-based molecular networking. Cultures were grown in a light- and temperature-controlled environment and harvested after several months of growth. The planar structure of pagoamide A (1) was characterized by detailed 1D and 2D NMR experiments along with MS and UV analysis. The absolute configurations of its amino acid residues were determined by advanced Marfey's analysis following chemical hydrolysis and hydrazinolysis reactions. Two of the residues in pagoamide A (1), phenylalanine and serine, each occurred twice in the molecule, once in the D- and once in the L-configuration. The biosynthetic origin of pagoamide A (1) was considered in light of other natural products investigations with coenocytic green algae.
• Coprisamides A and B, New Branched Cyclic Peptides from a Gut Bacterium of the Dung Beetle <i>Copris tripartitus</i>
  作者：Soohyun Um、So Hyun Park、Jihye Kim、Hyen Joo Park、Keebeom Ko、Hea-Son Bang、Sang Kook Lee、Jongheon Shin、Dong-Chan Oh

  DOI：10.1021/acs.orglett.5b00249

  日期：2015.3.6

  Coprisamides A and B (1 and 2) were isolated from a bacterium in the gut of the dung beetle Copris tripartitus. Spectroscopic analysis revealed that the planar structures of 1 and 2 are novel cyclic heptapeptides bearing unusual units, such as beta-methylaspartic acid and 2,3-diaminopropanoic acid branched to valine and 2-heptatrienyl cinnamic acid. Absolute configurations were established by chemical derivatization and chiroptical spectroscopy. The coprisamides displayed significant activity for induction of quinone reductase.
• Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle <i>Silpha perforata</i>
  作者：Yern-Hyerk Shin、Yeon Hee Ban、Tae Ho Kim、Eun Seo Bae、Jongheon Shin、Sang Kook Lee、Jichan Jang、Yeo Joon Yoon、Dong-Chan Oh

  DOI：10.1021/acs.jnatprod.0c00864

  日期：2021.2.26