(5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-D-phenylalanine | 95713-61-4

• 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: (5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-D-phenylalanine
• 英文别名: L-FDAA-D-Phe；FDAA-D-Phe
• CAS: 95713-61-4
• 化学式: C₁₈H₁₉N₅O₇
• 分子量: 417.378
• InChiKey: PVJKVUDESJPIAP-IINYFYTJSA-N

物化性质

• 沸点：
  772.5±60.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  在 盐酸 、 potassium permanganate 、 水 、 碳酸氢钠 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.55h， 生成 (5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-D-phenylalanine
  参考文献：
  名称：

  An Ugi-like Biosynthetic Pathway Encodes Bombesin Receptor Subtype-3 Agonists

  摘要：

  Isocyanide functional groups can be found in a variety of natural products. Rhabduscin is one such isocyanide-functionalized immunosuppressant produced in Xenorhabdus and Photorhabdus gammaproteobacterial pathogens, and deletion of its biosynthetic gene cluster inhibits virulence in an invertebrate animal infection model. Here, we characterized the first "opine-glycopeptide" class of natural products termed rhabdoplanins, and strikingly, these molecules are spontaneously produced from rhabduscin via an unprecedented multicomponent "Ugi-like" reaction sequence in nature. The rhabdoplanins also represent new lead G protein-coupled receptor (GPCR) agonists, stimulating the bombesin receptor subtype-3 (BB3) GPCR.

  DOI：

  10.1021/jacs.9b04183

文献信息

• Preparation of Chiral Amino Esters by Asymmetric Phase-Transfer Catalyzed Alkylations of Schiff Bases in a Ball Mill
  作者：Pierrick Nun、Violaine Pérez、Monique Calmès、Jean Martinez、Frédéric Lamaty

  DOI：10.1002/chem.201102885

  日期：2012.3.19

  The asymmetric alkylation of Schiff bases under basic conditions in a ball mill was performed. The starting Schiff bases of glycine were prepared beforehand by milling protected glycine hydrochloride and benzophenone imine, in the absence of solvent. The Schiff base was then reacted with a halogenated derivative in a ball mill in the presence of KOH. By adding a chiral ammonium salt derived from cinchonidine

  在球磨机中在碱性条件下进行席夫碱的不对称烷基化。甘氨酸的起始席夫碱是通过在没有溶剂的情况下将受保护的甘氨酸盐酸盐和二苯甲酮亚胺研磨而制备的。然后在KOH存在下，在球磨机中使席夫碱与卤代衍生物反应。通过添加衍生自辛可尼定的手性铵盐，该反应在相转移催化条件下不对称进行，获得了出色的收率，对映体过量高达75％。因为使用了等摩尔量的原料，所以大大简化了纯化。
• Zelkovamycin is an OXPHOS Inhibitory Member of the Argyrin Natural Product Family
  作者：Daniel Krahn、Geronimo Heilmann、Felix C. E. Vogel、Chrisovalantis Papadopoulos、Susanne Zweerink、Farnusch Kaschani、Hemmo Meyer、Alexander Roesch、Markus Kaiser

  DOI：10.1002/chem.202001577

  日期：2020.7.14

  diverse mode‐of‐action at the molecular level. By a combination of structure elucidation experiments, the first total synthesis of zelkovamycin and bioassays, the zelkovamycin configuration was determined and its previously proposed molecular structure was revised. The full structure assignment proves zelkovamycin as an additional member of the argyrins with however unique OXPHOS inhibitory properties

  天然产物（NPs）是开发药物和化学探针的重要灵感来源。1999年，Ōmura小组报告了对zelkovamycin的宪法解释。尽管目前为止尚未被广泛认识，但该NP与精蛋白NP家族具有结构相似性和差异，后者是一类肽NP，在分子水平上具有抗癌活性和不同的作用方式。通过结合结构阐明实验，首次合成合成的zelkovamycin和生物测定法，确定了zelkovamycin的构型并修改了其先前提出的分子结构。完整的结构证明佐科霉素是精氨酸的另一成员，具有独特的OXPHOS抑制特性。
• α-Pyrones and Diketopiperazine Derivatives from the Marine-Derived Actinomycete Nocardiopsis dassonvillei HR10-5
  作者：Peng Fu、Peipei Liu、Haijun Qu、Yi Wang、Dianfeng Chen、Hui Wang、Jing Li、Weiming Zhu

  DOI：10.1021/np200597m

  日期：2011.10.28

  Three new α-pyrones, nocapyrones E–G (1–3), and three new diketopiperazine derivatives, nocazines A–C (4–6), together with a new oxazoline compound, nocazoline A (7), were isolated from the marine-derived actinomycete Nocardiopsis dassonvillei HR10-5. The new structures of 1–7 were determined by spectroscopic analysis, X-ray single-crystal diffraction, CD spectra, and modified Mosher and Marfey methods

  三个新的α吡喃酮，nocapyrones E-G（1 - 3），并且三个新的二酮哌嗪衍生物，nocazines A-C（4 - 6），加上一个新的恶唑啉化合物，nocazoline A（7），从海洋中分离来源的放线菌诺卡氏菌达森氏菌HR10-5。的新的结构1 - 7是由分光分析，X射线单晶衍射，CD谱确定，和改性的莫舍和的Marfey方法。化合物1 - 3显示针对适度的抗微生物活性的枯草芽孢杆菌与26，14，和12μM的MIC值，分别。
• New phenethylamine derivatives from Arenibacter nanhaiticus sp. nov. NH36AT and their antimicrobial activity
  作者：Yanping Chen、Jinshan Tang、Xixiang Tang、Chuanxi Wang、Yunyang Lian、Zongze Shao、Xinsheng Yao、Hao Gao

  DOI：10.1038/ja.2013.65

  日期：2013.11

  Five new phenethylamine (PEA) derivatives (1–5) were isolated from the strain of Arenibacter nanhaiticus sp. nov. NH36AT derived from the marine sediment of the South China Sea by bioassay-guided fractionation. Their structures were elucidated by spectroscopic methods including UV, IR, HR-MS and NMR. Interestingly, compounds 1–4 existed as enantiomers, which were resolved by chiral liquid chromatography. The resolved configuration of each enantiomer was assigned by the Marfey’s method. Of these compounds, 5 showed weak antimicrobial activity against Staphylococcus aureus and Bacillus subtilis with MIC values of 0.50 and 0.25 mg ml−1, respectively.

  通过生物测定导向分离，从南海海洋沉积物中分离出的新种NH36AT菌株中分离得到5个新的苯乙胺(PEA)衍生物(1-5)。通过光谱方法包括紫外、红外、高分辨质谱和核磁共振对其结构进行了鉴定。有趣的是，化合物1-4以对映异构体的形式存在，通过手性液相色谱进行了分离。每个对映异构体的构型通过Marfey法进行了确定。在这些化合物中，5号化合物对金黄色葡萄球菌和枯草芽孢杆菌显示出弱抗菌活性，最小抑菌浓度(MIC)值分别为0.50和0.25 mg/ml。
• Streptopyrazinones A−D, rare metabolites from marine-derived Streptomyces sp. ZZ446
  作者：Mengxuan Chen、Weiyun Chai、Rongyao Zhu、Tengfei Song、Zhizhen Zhang、Xiao-Yuan Lian

  DOI：10.1016/j.tet.2018.03.028

  日期：2018.4

  Secondary metabolites from marine-associated actinomycetes are important source for the discovery of novel bioactive compounds. In this study, an actinomycete Streptomyces sp. ZZ446 was isolated from coastal soils and different media were used to culture this isolated marine actinomycete. It has been found that this actinomycete in the liquid medium of 2216 E with sea salt produced five new compounds of streptopyrazinones

  来自海洋相关放线菌的次生代谢产物是发现新型生物活性化合物的重要来源。在这项研究中，放线菌Streptomyces sp。ZZ446是从沿海土壤中分离出来的，使用不同的培养基来培养这种分离的海洋放线菌。已经发现，该放线菌在2216ë海盐的液体培养基中生产streptopyrazinones五个新化合物A-d（1 - 4）和Ñ乙酰基升-isoleucine-升-leucinamide（5）以及6个已知的二酮哌嗪（6 – 11）和一种生物碱（12）。通过广泛的NMR分析，HRESIMS数据，电子圆二色性（ECD）计算，化学降解，Marfey方法和X射线衍射分析确定了新化合物的结构。这种类型streptopyrazinones A-d（的1 - 4）在自然资源，很难找到。新的化合物1 - 5抑制生长显示活性白色念珠菌和耐甲氧西林金黄色葡萄球菌。