FDAA-D-NMe-Val | 194736-84-0

• 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: FDAA-D-NMe-Val
• CAS: 194736-84-0
• 化学式: C₁₅H₂₁N₅O₇
• 分子量: 383.361
• InChiKey: SZIMHYAZLLJHLK-ISVAXAHUSA-N

反应信息

• 作为产物：
  描述：

  N-甲基-D-缬氨酸 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 FDAA-D-NMe-Val
  参考文献：
  名称：

  天然产物中氨基酸分析的C 3和2D C 3 Marfey方法

  摘要：

  我们验证了C 3 Marfey方法的改进的分辨率和灵敏度，包括针对天然产物中常见的一系列氨基酸并通过与现有Marfey方法进行比较而解决所有Ile异构体的能力。我们还描述了一种创新的二维C 3 Marfey方法，作为一种确定天然产物中对映体氨基酸残基的区域化学的分析方法。C 3和2 D C 3 Marfey的方法代表了宝贵的工具，可用于探测和定义天然产物中可水解获得的氨基酸残基的立体复杂性。

  DOI：

  10.1021/acs.jnatprod.5b01125

文献信息

• Evolved Diversification of a Modular Natural Product Pathway: Apratoxins F and G, Two Cytotoxic Cyclic Depsipeptides from a Palmyra Collection of Lyngbya bouillonii
  作者：Kevin Tidgewell、Niclas Engene、Tara Byrum、Joseph Media、Takayuki Doi、Fred A. Valeriote、William H. Gerwick

  DOI：10.1002/cbic.201000070

  日期：——

  Tropical cytotoxin: A collection of Lyngbya bouillonii from Palmyra Atoll in the Central Pacific, a site several thousand kilometers distant from all previous collections of this chemically prolific species of cyanobacterium, was found to contain two new cancer cell cytotoxins of the apratoxin family.

  热带细胞毒素：发现来自中太平洋巴尔米拉环礁的Lyngbya bouillonii的集合，该地点距离这种化学多产的蓝藻物种的所有先前集合数千公里，被发现含有两种新的 apratoxin 家族的癌细胞细胞毒素。
• A New Analogue of Echinomycin and a New Cyclic Dipeptide from a Marine-Derived Streptomyces sp. LS298
  作者：Xin Zhen、Ting Gong、Fu Liu、Pei-Cheng Zhang、Wan-Qi Zhou、Yan Li、Ping Zhu

  DOI：10.3390/md13116947

  日期：——

  Quinomycin G (1), a new analogue of echinomycin, together with a new cyclic dipeptide, cyclo-(l-Pro-4-OH-l-Leu) (2), as well as three known antibiotic compounds tirandamycin A (3), tirandamycin B (4) and staurosporine (5), were isolated from Streptomyces sp. LS298 obtained from a marine sponge Gelliodes carnosa. The planar and absolute configurations of compounds 1 and 2 were established by MS, NMR spectral data analysis and Marfey’s method. Furthermore, the differences in NMR data of keto-enol tautomers in tirandamycins were discussed for the first time. Antibacterial and anti-tumor activities of compound 1 were measured against 15 drug-sensitive/resistant strains and 12 tumor cell lines. Compound 1 exhibited moderate antibacterial activities against Staphylococcuse pidermidis, S. aureus, Enterococcus faecium, and E. faecalis with the minimum inhibitory concentration (MIC) values ranged from 16 to 64 μg/mL. Moreover, it displayed remarkable anti-tumor activities; the highest activity was observed against the Jurkat cell line (human T-cell leukemia) with an IC50 value of 0.414 μM.

  从海洋海绵 Gelliodes carnosa 中获得的链霉菌 LS298 中分离出了棘霉素的新类似物喹诺霉素 G (1)、一种新的环状二肽环-(l-Pro-4-OH-l-Leu) (2)，以及三种已知的抗生素化合物 tirandamycin A (3)、tirandamycin B (4) 和 staurosporine (5)。通过质谱、核磁共振光谱数据分析和马菲法，确定了化合物 1 和 2 的平面构型和绝对构型。此外，还首次讨论了替兰达霉素酮烯醇同分异构体核磁共振数据的差异。化合物 1 针对 15 种药物敏感/耐药菌株和 12 种肿瘤细胞系进行了抗菌和抗肿瘤活性测定。化合物 1 对表皮葡萄球菌、金黄色葡萄球菌、粪肠球菌和粪大肠杆菌具有中等程度的抗菌活性，最低抑菌浓度 (MIC) 值介于 16 至 64 μg/mL 之间。此外，它还显示出显著的抗肿瘤活性；对 Jurkat 细胞系（人类 T 细胞白血病）的活性最高，IC50 值为 0.414 μM。
• Friomaramide, a Highly Modified Linear Hexapeptide from an Antarctic Sponge, Inhibits <i>Plasmodium falciparum</i> Liver-Stage Development
  作者：Matthew A. Knestrick、Nerida G. Wilson、Alison Roth、John H. Adams、Bill J. Baker

  DOI：10.1021/acs.jnatprod.9b00362

  日期：2019.8.23

  The cold waters of Antarctica are known to harbor a rich biodiversity. Our continuing interest in the chemical analysis of Antarctic invertebrates has resulted in the isolation of friomaramide (1), a new, highly modified hexapeptide, from the Antarctic sponge Inflatella coelosphaeroides. The structure of friomaramide was determined using spectroscopic methods and its configuration established by Marfeys method. Friomaramide, which bears the unusual permethylation of the amino acid backbone and is the longest polypeptide bearing a tryptenamine C-terminus, blocks >90% of Plasmodium falciparum liver-stage parasite development at 6.1 mu M.
• Suberoylanilide Hydroxamic Acid, a Histone Deacetylase Inhibitor, Induces the Production of Anti-inflammatory Cyclodepsipeptides from <i>Beauveria felina</i>
  作者：Yu-Ming Chung、Mohamed El-Shazly、Da-Wei Chuang、Tsong-Long Hwang、Teigo Asai、Yoshiteru Oshima、Mohamed L. Ashour、Yang-Chang Wu、Fang-Rong Chang

  DOI：10.1021/np400143j

  日期：2013.7.26

  The addition of the histone deacetylase inhibitor suberoylanilide hydroxamic acid to a culture of the filamentous fungus Beauveria felina significantly changed its secondary metabolite profile and led to the isolation of eight compounds, including three new cyclodepsipeptides, desmethylisaridin E (1), desmethylisaridin C2 (2), and isaridin F (3), along with five known cyclodepsipeptide compounds. Isaridin F (3) possesses a cyclodepsipeptide ring with N-methylbutyric acid, which is rare in natural peptides. Absolute configurations of the new cyclodepsipeptides were achieved by Marfey's method. The anti-inflammatory activity of the isolated compounds was investigated through evaluating their effect on superoxide anion production and elastase release by FMLP-induced human neutrophils. Among the tested compounds, desmethylisaridin E (1) inhibited superoxide anion production and desmethylisaridin C2 (2) inhibited elastase release, with IC50 values of 10.00 +/- 0.80 and 10.01 +/- 0.46 mu M, respectively.
• Persipeptides A and B, two cyclic peptides from Streptomyces sp. UTMC 1154
  作者：Fatemeh Mohammadipanah、Josphat Matasyoh、Javad Hamedi、Hans-Peter Klenk、Hartmut Laatsch

  DOI：10.1016/j.bmc.2011.10.076

  日期：2012.1

  Two new N-methylated cyclopeptides, persipeptide A (1) and B (2), have been isolated from Streptomyces sp. UTMC1154. Their structures were established using 1D and 2D NMR experiments. 2D TOCSY experiments were applied to identify the amino acid residues, while HMBC correlations were used to determine their sequence. According to Marfey's method, all amino acids had the L-configuration. The two cyclic peptides had the same ring size and amino acid composition, but differed in their sequence; they did not show activity against the tested bacteria, fungi and algae. Molecular identification experiments placed the strain in the genus Streptomyces closely related to Streptomyces coerulescens DSM40146(T) (99.45%) and Streptomyces varsoviensis DSM40346(T) (99.25%). (C) 2011 Elsevier Ltd. All rights reserved.