L-FDAA-D-N-methylalanine | 194736-82-8

• 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: L-FDAA-D-N-methylalanine
• 英文别名: FDAA-D-NMe-Ala；D-Me-Ala-FDAA
• CAS: 194736-82-8
• 化学式: C₁₃H₁₇N₅O₇
• 分子量: 355.307
• InChiKey: HIXQVPVKBYRNSK-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  181.94
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  N-甲基-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 丙酮 为溶剂， 反应 1.5h， 生成 L-FDAA-D-N-methylalanine
  参考文献：
  名称：

  使用基于 LC-MS/MS 的分子网络从真菌 Aspergillus westerdijkiae 中提取具有协同抗真菌活性的环状四肽

  摘要：

  真菌天然产物在药物制剂的开发中发挥着突出的作用。在 OSMAC（一株多种化合物）和分子网络策略的指导下，从真菌 Aspergillus westerdijkiae 中分离出两种新的环状四肽 (CTP)、westertide A (1) 和 B (2)，以及八种已知化合物 (3-10)。通过核磁共振和质量数据分析以及化学方法的结合，明确确定了新化合物的结构。对所有分离株的抗菌作用、协同抗真菌活性、细胞毒活性和 HDAC 抑制活性进行了评估。化合物 1-2 对白色念珠菌 SC5314 表现出协同抗真菌活性，且存在雷帕霉素和弱 HDAC（组蛋白脱乙酰酶）抑制活性。这些结果表明分子网络是去重复和识别新 CTP 的有效方法。 CTP 可能是开发协同抗真菌药物的良好起点。

  DOI：

  10.3390/antibiotics11020166

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。
• Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.
  作者：Kosuke Sueyoshi、Masato Kaneda、Shinpei Sumimoto、Shinya Oishi、Nobutaka Fujii、Kiyotake Suenaga、Toshiaki Teruya

  DOI：10.1016/j.tet.2016.07.031

  日期：2016.9

  The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the 26-membered cyclodepsipeptide odoamide (1). The gross structure of 1 was determined by 1D and 2D NMR analyses, whereas its absolute stereochemistry was determined using a variety of different methods, including synthesis and chemical degradation followed by chiral HPLC analysis. Notably,

  冲绳海洋蓝藻Okeania sp。的生物测定指导分馏。导致分离出26元的环二肽肽odamide（1）。的总体结构1是由一维测定和二维NMR分析，而是使用各种不同的方法，包括合成和化学降解，然后通过手性HPLC分析测定其绝对立体化学。值得注意的是，odoamide（1）对HeLa S3人宫颈癌细胞具有强大的细胞毒性，IC 50值为26.3 nM。
• Two New Cyclic Pentapeptides from the Marine-Derived Fungus Aspergillus versicolor
  作者：Li-Na Zhou、Hu-Quan Gao、Sheng-Xin Cai、Tian-Jiao Zhu、Qian-Qun Gu、De-Hai Li

  DOI：10.1002/hlca.201000408

  日期：2011.6

  Two new cyclic pentapeptides, named versicotides A (1) and B (2), were obtained from a marine‐derived fungus strain ZLN‐60, identified as Aspergillus versicolor. Their structures were established on the basis of chemical and spectroscopic evidence. Versicotides are new cyclic pentapeptides which contain an L‐alanine residue, two anthranilic acid (=2‐aminobenzoic acid) residues, and two N‐methyl‐L‐alanine

  从海洋衍生的真菌菌株ZLN-60（称为杂色曲霉）中获得了两个新的环状五肽，分别为versicotides A（1）和B（2）。它们的结构是根据化学和光谱学证据建立的。Versicotides是新的环状五肽，包含L-丙氨酸残基，两个邻氨基苯甲酸（= 2-氨基苯甲酸）残基和两个N-甲基-L-丙氨酸残基。通过SRB和MTT方法评估抗肿瘤活性。
• 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.
• Psychrophilins E–H and Versicotide C, Cyclic Peptides from the Marine-Derived Fungus <i>Aspergillus versicolor</i> ZLN-60
  作者：Jixing Peng、Huquan Gao、Xiaomin Zhang、Shuai Wang、Chongming Wu、Qianqun Gu、Peng Guo、Tianjiao Zhu、Dehai Li

  DOI：10.1021/np500469b

  日期：2014.10.24

  Four new cyclic peptides, psychrophilins E-H (1-4), possessing a rare amide linkage between the carboxylic acid in anthranilic acid (ATA) and the nitrogen from an indole moiety, along with a new ATA-containing hexapeptide, versicotide C (5), were obtained from the culture of the marine-derived fungus Aspergillus versicolor ZLN-60. The structures, including absolute configurations, were elucidated by a combination of HRESIMS, NMR, X-ray crystallography, TDDFT ECD calculations, and Marfey's method. Versicotide C (5) is the first natural cyclic hexapeptide containing two anthranilic acids. Compounds 1-5 were not cytotoxic, and compound 3 showed potent lipid-lowering effects.