D-FDAA-L-Ala | 194737-01-4

• 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: D-FDAA-L-Ala
• 英文别名: L-alanine-D-FDAA
• CAS: 194737-01-4
• 化学式: C₁₂H₁₅N₅O₇
• 分子量: 341.28
• InChiKey: QMGXWWJTXPWIMG-RITPCOANSA-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 、 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， 生成 D-FDAA-L-Ala
  参考文献：
  名称：

  Cyclotheonellazos DI，来自 Theonella sp. 的有效弹性蛋白酶抑制含噻唑环肽。(2131)

  摘要：

  从澳大利亚海洋海绵Theonella sp . 中分离出六种新的含噻唑环肽，即 cyclotheonellazos D–I ( 1 – 6 ) 。(2131) 其结构通过综合一维和二维核磁共振波谱和质谱分析、Marfey 的衍生化研究以及与时间相关密度泛函理论 (TDDFT) 计算的 ECD 数据的比较来确定。本文的 2 型唑同系肽包含多达 5 个非蛋白氨基酸，包括蛋白酶过渡态模拟 α-酮-β-氨基酸残基 3-氨基-4-甲基-2-氧代己酸 (Amoha)，而1 – 3还含有以前在环噻唑啉中未发现的末端乙内酰脲残基。重新分离了角酰胺 A ( 7 ) 和 L ( 8 )，从而扩大了对其生物活性的探索。检查了这些肽对两种哺乳动物丝氨酸蛋白酶（弹性蛋白酶和胰凝乳蛋白酶）和 SARS-CoV-2 3-胰凝乳蛋白酶样蛋白酶（3CL pro）的蛋白酶抑制活性，后者是经过验证的 COVID-19 抗病毒治疗靶点。肽1

  DOI：

  10.1021/acs.jnatprod.3c00633

文献信息

• Pembamide, a N -methylated linear peptide from a sponge Cribrochalina sp.
  作者：Carlos Urda、Marta Pérez、Jaime Rodríguez、Carlos Jiménez、Carmen Cuevas、Rogelio Fernández

  DOI：10.1016/j.tetlet.2016.05.054

  日期：2016.7

  A new highly N-methylated linear peptide, pembamide (1), has been isolated from the marine sponge Cribrochalina sp. (family Niphatidae) collected off the coast of Pemba (Tanzania). The planar structure of 1 was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configuration of the amino acid residues in 1 was determined by application of the Advanced

  从海洋海绵Cribrochalina sp。中分离到一种新的高N-甲基化线性肽pembamide（1）。（家庭Niphatidae）收集了奔巴（坦桑尼亚）的沿海。的平面结构1被分配了广泛1D和2D NMR光谱和质谱的基础上。应用Advanced Marfey法测定1中氨基酸残基的绝对构型。化合物1对三种人类肿瘤细胞系表现出明显的细胞毒性，其GI 50值在微摩尔范围内。
• C₃ and 2D C₃ Marfey’s Methods for Amino Acid Analysis in Natural Products
  作者：Soumini Vijayasarathy、Pritesh Prasad、Leith J. Fremlin、Ranjala Ratnayake、Angela A. Salim、Zeinab Khalil、Robert J. Capon

  DOI：10.1021/acs.jnatprod.5b01125

  日期：2016.2.26

  Marfey’s method, including an ability to resolve all Ile isomers, against an array of amino acids commonly encountered in natural products and by comparison to an existing Marfey’s method. We also describe an innovative 2D C3 Marfey’s method as an analytical approach for determining the regiochemistry of enantiomeric amino acid residues in natural products. The C3 and 2D C3 Marfey’s methods represent

  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。
• Lagunamide C, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Lyngbya majuscula
  作者：Ashootosh Tripathi、Jonathan Puddick、Michele R. Prinsep、Matthias Rottmann、Kok Ping Chan、David Yu-Kai Chen、Lik Tong Tan

  DOI：10.1016/j.phytochem.2011.08.019

  日期：2011.12

  Lagunamide C (1) is a cytotoxic cyclodepsipeptide isolated from the marine cyanobacterium, Lyngbya majuscula, from the western lagoon of Pulau Hantu Besar, Singapore. The complete structural characterization of the molecule was achieved by extensive NMR spectroscopic analysis as well as chemical manipulations. Several methods, including the advanced Marfey's method, a modified method based on derivatization

  Lagunamide C (1) 是一种细胞毒性环缩肽，从来自新加坡汉都岛西部泻湖的海洋蓝藻 Lyngbya majuscula 中分离出来。分子的完整结构表征是通过广泛的 NMR 光谱分析以及化学操作实现的。几种方法，包括先进的 Marfey 方法，一种基于 Mosher 试剂衍生化和使用 LC-MS 分析的改进方法，以及 (3)J(HH) 耦合常数值的使用，用于确定其绝对构型。化合物 1 与 aurilide 类分子有关，它的主要区别在于大环结构的不同之处在于由于聚酮化合物部分中额外的亚甲基碳而具有 27 元环系统。Lagunamide C 对一组癌细胞系（如 P388、A549、PC3、HCT8 和 SK-OV3 细胞系）显示出有效的细胞毒活性，IC(50) 值范围为 2.1 nM 到 24.4 nM。当针对恶性疟原虫进行测试时，化合物 1 还显示出显着的抗疟活性，IC(50) 值为
• 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.
• Lipopeptides from the Tropical Marine Cyanobacterium <i>Symploca</i> sp.
  作者：Emily Mevers、F. P. Jake Haeckl、Paul D. Boudreau、Tara Byrum、Pieter C. Dorrestein、Frederick A. Valeriote、William H. Gerwick

  DOI：10.1021/np401051z

  日期：2014.4.25

  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.