(2S)-2-[(5-氟-2,4-二硝基苯基)氨基]丙酸 | 346-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2S)-2-[(5-氟-2,4-二硝基苯基)氨基]丙酸
• 中文别名: 1-{4-[(6-氯-1H-苯并咪唑-2-基)甲氧基]苯基}-3-(4-甲基苯基)硫代脲
• 英文名称: N-α-5-fluoro-2,4-dinitrophenyl-5-L-alanineamide
• 英文别名: 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide；1-fluoro-2,4-dinitrophenyl-5-L-alaninamide；Marfey's reagent；L-FDAA；FDAA；1-Fluoro-2,4-dinitrophenyl-5-alanine；(2S)-2-(5-fluoro-2,4-dinitroanilino)propanoic acid
• CAS: 346-48-5
• 化学式: C₉H₈FN₃O₆
• 分子量: 273.177
• InChiKey: WLZJKCUZPMEFKC-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-别苏氨酸 、 (2S)-2-[(5-氟-2,4-二硝基苯基)氨基]丙酸 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 生成 L-FDAA-L-allo-Thr
  参考文献：
  名称：

  Lahorenoic Acids A–C, ortho-Dialkyl-Substituted Aromatic Acids from the Biocontrol Strain Pseudomonas aurantiaca PB-St2

  摘要：

  Three new aromatic acids, named lahorenoic acids A (1), B (2), and C (3), have been isolated along with the known compounds phenazine-1-carboxylic acid (4), 2-hydroxyphenazine-1-carboxylic acid (5), 2-hydroxyphenazine (6), 2,8-dihydroxyphenazine (7), cyclo-Pro-Tyr (8), cyclo-Pro-Val (9), cyclo-Pro-Met (10), and WLIP (11) and characterized from the biocontrol strain Pseudomonas aurantiaca PB-St2. The structures of these compounds were deduced by 1D and 2D NMR spectroscopic and mass spectral data interpretation. Compounds 2, 4, and 7 showed moderate antibacterial activity against mycobacteria and other Gram-positive bacteria, while 4 was also found to exhibit cytotoxic and antifungal properties.

  DOI：

  10.1021/np3005166

文献信息

• Bioactive Phenylalanine Derivatives and Cytochalasins from the Soft Coral-Derived Fungus, Aspergillus elegans
  作者：Cai-Juan Zheng、Chang-Lun Shao、Lu-Yong Wu、Min Chen、Kai-Ling Wang、Dong-Lin Zhao、Xue-Ping Sun、Guang-Ying Chen、Chang-Yun Wang

  DOI：10.3390/md11062054

  日期：——

  One new phenylalanine derivative 4'-OMe-asperphenamate (1), along with one known phenylalanine derivative (2) and two new cytochalasins, aspochalasin A1 (3) and cytochalasin Z24 (4), as well as eight known cytochalasin analogues (5-12) were isolated from the fermentation broth of Aspergillus elegans ZJ-2008010, a fungus obtained from a soft coral Sarcophyton sp. collected from the South China Sea.

  一种新的苯丙氨酸衍生物 4'-OMe-asperphenamate (1)，以及一种已知的苯丙氨酸衍生物 (2) 和两种新的细胞松弛素，aspochalasin A1 (3) 和细胞松弛素 Z24 (4)，以及八种已知的细胞松弛素类似物 (5- 12) 是从线虫 ZJ-2008010 的发酵液中分离出来的，这是一种从软珊瑚 Sarcophyton sp. 获得的真菌。采集自南海。使用综合光谱方法阐明了它们的结构和相关构型。1 的绝对构型是通过化学合成和 Marfey 方法确定的。评估了所有分离的代谢物 (1-12) 的防污和抗菌活性。Cytochalasins 5、6、8 和 9 对藤壶 Balanus amphitrite 的幼虫沉降显示出很强的防污活性，EC50 值范围为 6.2 至 37 μM。这是此类代谢物防污活性的第一份报告。此外，8 表现出广谱的抗菌活性，特别是对四种病原菌白色
• Salinipeptins: Integrated Genomic and Chemical Approaches Reveal Unusual <scp>d</scp>-Amino Acid-Containing Ribosomally Synthesized and Post-Translationally Modified Peptides (RiPPs) from a Great Salt Lake <i>Streptomyces</i> sp.
  作者：Zhuo Shang、Jaclyn M. Winter、Christopher A. Kauffman、Inho Yang、William Fenical

  DOI：10.1021/acschembio.8b01058

  日期：2019.3.15

  unprecedented linaridins bearing nine d-amino acids, which are uncommon in RiPP natural products and are the first reported in the linaridin subfamily. Whole genome mining of GSL-6C did not reveal any homologues of the reported genes responsible for amino acid epimerization in RiPPs, inferring new epimerases may be involved in the conversion of l- to d-amino acids. In addition, the N-oxide and dimethylimidazolidin-4-one

  分析一个环境独特的卤代链霉菌sp。的完整基因组。从大盐湖中分离出的GSL-6C菌株揭示了一个基因簇，该基因簇编码了salipipeptins的生物合成，该salinipeptins是核糖体合成的稀有亚麻油蛋白亚家族成员的d-氨基酸，并具有翻译后修饰的肽（RiPPs）。通过基因组注释建议了salinipeptins AD（1-4）中未修饰氨基酸残基的序列组织，随后，使用一系列光谱技术和化学衍生方法定义了它们的序列和翻译后修饰。salinipeptins是带有9个d-氨基酸的空前的亚麻籽蛋白，在RiPP天然产物中并不常见，并且是亚麻籽蛋白亚家族中的第一个报道。GSL-6C的全基因组挖掘未发现RiPPs中负责氨基酸差向异构化的报道基因的任何同源物，推测新的差向异构酶可能参与了从1-到d-氨基酸的转化。另外，在细菌肽中未知由N，N-二甲基丙氨酸修饰的盐肽素B和C中的N-氧化物和二甲基咪唑啉丁-4-
• Development and Scale-up of an Organocatalytic Enantioselective Process to Manufacture (<i>S</i>)-Pregabalin
  作者：Maria Moccia、Mauro Cortigiani、Claudio Monasterolo、Federica Torri、Claudia Del Fiandra、Geoffrey Fuller、Brian Kelly、Mauro F. A. Adamo

  DOI：10.1021/acs.oprd.5b00160

  日期：2015.9.18

  Herein is reported the development of a new process to manufacture (S)-pregabalin. The method comprises six steps, run under the catalysis of a recyclable polymer bound phase transfer catalyst, and afforded (S)-pregabalin in overall 54% yield, starting from building blocks acetylacetone, isovaleraldehyde, and nitromethane.
• Synthesis of poly (γ-glutamic acid) and heterologous expression of pgsBCA genes
  作者：Mingfeng Cao、Cunjiang Song、Yinghong Jin、Li Liu、Jing Liu、Hui Xie、Wenbin Guo、Shufang Wang

  DOI：10.1016/j.molcatb.2010.07.014

  日期：2010.11

  The genes required for synthesis of poly (gamma-glutamic acid) (gamma-PGA) were cloned from Bacillus licheniformis NK-03, a strain isolated from fermented food, natto. There were three open reading frames pgsB, pgsC, pgsA in the cloned fragment, all of which were greatly similar with those from typical Bacillus subtilis strains. The alignment of deduced amino acid sequences showed that PgsC was the most conservative part in PgsBCA. Recombinant plasmid pXMJ19-PGS was constructed by a shuttle vector pXMJ19, and it was successfully transformed and expressed in the recombinant strains of Escherichia coli JM109 and Corynebacterium glutamicum ATCC13032, respectively. Expression of pgsBCA in C. glutamicum indicated that it could synthesize gamma-PGA with a yield of 0.69 g/L and 97% proportion of L-glutamate monomer in the absence of glutamic acid. The results suggest that gamma-PGA biosynthesis directly from glucose by genetic engineering is feasible and significant. (C) 2010 Elsevier B.V. All rights reserved.
• Lahorenoic Acids A–C, <i>ortho</i>-Dialkyl-Substituted Aromatic Acids from the Biocontrol Strain <i>Pseudomonas aurantiaca</i> PB-St2
  作者：Samina Mehnaz、Rahman Shah Zaib Saleem、Basit Yameen、Isabelle Pianet、Gregor Schnakenburg、Halina Pietraszkiewicz、Fred Valeriote、Michaele Josten、Hans-Georg Sahl、Scott G. Franzblau、Harald Gross

  DOI：10.1021/np3005166

  日期：2013.2.22

  Three new aromatic acids, named lahorenoic acids A (1), B (2), and C (3), have been isolated along with the known compounds phenazine-1-carboxylic acid (4), 2-hydroxyphenazine-1-carboxylic acid (5), 2-hydroxyphenazine (6), 2,8-dihydroxyphenazine (7), cyclo-Pro-Tyr (8), cyclo-Pro-Val (9), cyclo-Pro-Met (10), and WLIP (11) and characterized from the biocontrol strain Pseudomonas aurantiaca PB-St2. The structures of these compounds were deduced by 1D and 2D NMR spectroscopic and mass spectral data interpretation. Compounds 2, 4, and 7 showed moderate antibacterial activity against mycobacteria and other Gram-positive bacteria, while 4 was also found to exhibit cytotoxic and antifungal properties.