(5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-L-glutamic acid | 95713-56-7

• 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)-L-glutamic acid
• 英文别名: L-DAA-glu
• CAS: 95713-56-7
• 化学式: C₁₄H₁₇N₅O₉
• 分子量: 399.317
• InChiKey: XISGXMPEFWFHIS-BQBZGAKWSA-N

物化性质

• 沸点：
  809.7±65.0 °C(Predicted)
• 密度：
  1.650±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  228.03
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  5'-[2-(S)-N-benzyloxy-N-(fluorenylmethyloxycarbonylaminoacetyl)amino-4-cyanobutanoylamino]-5'-deoxypseudouridine 在 indium(III) chloride 、 乙醛肟 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 66.0h， 生成 (5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-L-glutamic acid
  参考文献：
  名称：

  Ugi型多组分反应全合成假尿嘧啶及其差向异构体

  摘要：

  完成了假尿嘧啶 ( 1 )的全合成，其特征在于不寻常的肟 Ugi 型多组分缩合以同时构建这种肽基核苷抗生素的二肽部分。在这个合成路线1中，通过假尿苷的9 个合成步骤的最长线性序列很容易获得。该策略可适用于多种假尿嘧啶类似物。

  DOI：

  10.1039/d2cc02442j

文献信息

• 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。
• Cyclic lipodepsipeptides verlamelin A and B, isolated from entomopathogenic fungus Lecanicillium sp.
  作者：Kei-ichi Ishidoh、Hiroshi Kinoshita、Yasuhiro Igarashi、Fumio Ihara、Takuya Nihira

  DOI：10.1038/ja.2014.22

  日期：2014.6

  Verlamelin and its new derivative (verlamelin B) were isolated from fermentation broth of entomopathogenic fungus Lecanicillium sp. HF627. As the structural elucidation of verlamelin so far was only preliminary, we studied and determined the absolute structure of these two compounds to be cyclo(5S-hydroxytetradecanoic acid-D-alloThr/Ser-D-Ala-L-Pro-L-Gln-D-Tyr-L-Val). This is the first study that precisely analyzed the structure of verlamelin.

  来源于昆虫病原真菌Lecanicillium sp. HF627的发酵液中分离得到韦拉霉素及其新衍生物（韦拉霉素B）。由于目前对韦拉霉素的结构阐述仅是初步的，我们对其进行了研究并确定了这两种化合物的绝对构型为环状（5S-羟基十四酸-D-别苏氨酸/丝氨酸-D-丙氨酸-L-脯氨酸-L-谷氨酰胺-D-酪氨酸-L-缬氨酸）。这是首次对韦拉霉素结构进行精确分析的研究。
• 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。
• Seven New and Two Known Lipopeptides as well as Five Known Polyketides: The Activated Production of Silent Metabolites in a Marine-Derived Fungus by Chemical Mutagenesis Strategy Using Diethyl Sulphate
  作者：Chang-Jing Wu、Chang-Wei Li、Cheng-Bin Cui

  DOI：10.3390/md12041815

  日期：——

  AD-2-1 is an antitumor fungal mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59. The G59 strain originally did not produce any metabolites with antitumor activities in MTT assays using K562 cells. Tracing newly produced metabolites under guidance of MTT assay and TLC analysis by direct comparison with control G59 extract, seven new (1–7) and two known (8–9) lipopeptides were isolated together with five known polyketides 10–14 from the extract of mutant AD-2-1. Structures of the seven new compounds including their absolute configurations were determined by spectroscopic and chemical evidences and named as penicimutalides A–G (1–7). Seven known compounds were identified as fellutamide B (8), fellutamide C (9), 1′-O-methylaverantin (10), averantin (11), averufin (12), nidurufin (13), and sterigmatocystin (14). In the MTT assay, 1–14 inhibited several human cancer cell lines to varying extents. All the bioassays and HPLC-photodiode array detector (PDAD)-UV and HPLC-electron spray ionization (ESI)-MS analyses demonstrated that the production of 1–14 in the mutant AD-2-1 was caused by the activated production of silent metabolites in the original G59 fungal strain. Present results provided additional examples for effectiveness of the chemical mutagenesis strategy using diethyl sulphate mutagenesis to discover new compounds by activating silent metabolites in fungal isolates.

  AD-2-1 是一种抗肿瘤真菌突变体，它是通过硫酸二乙酯诱变海洋源青霉菌 G59 获得的。在使用 K562 细胞进行的 MTT 试验中，G59 菌株原本不产生任何具有抗肿瘤活性的代谢物。在 MTT 试验和 TLC 分析的指导下，通过与对照 G59 提取物的直接比较，对新产生的代谢物进行了追踪，从突变体 AD-2-1 的提取物中分离出了七种新的（1-7）和两种已知的（8-9）脂肽，以及五种已知的多酮类化合物 10-14。通过光谱和化学证据确定了七种新化合物的结构及其绝对构型，并将其命名为青霉酰胺 A-G（1-7）。七个已知化合物被鉴定为fellutamide B (8)、fellutamide C (9)、1′-O-methylaverantin (10)、averantin (11)、averufin (12)、nidurufin (13) 和 sterigmatocystin (14)。在 MTT 试验中，1-14 对几种人类癌细胞株有不同程度的抑制作用。所有生物测定和高效液相色谱-光电二极管阵列检测器（PDAD）-紫外和高效液相色谱-电子喷雾电离（ESI）-质谱分析表明，突变体 AD-2-1 中 1-14 的产生是由原始 G59 真菌菌株中沉默代谢物的活化产生引起的。本研究结果为利用硫酸二乙酯诱变的化学诱变策略通过激活真菌分离物中的沉默代谢物来发现新化合物的有效性提供了更多实例。
• Phenylspirodrimanes with Anti-HIV Activity from the Sponge-Derived Fungus <i>Stachybotrys chartarum</i> MXH-X73
  作者：Xinhua Ma、Letao Li、Tianjiao Zhu、Mingyu Ba、Guoqiang Li、Qianqun Gu、Ying Guo、Dehai Li

  DOI：10.1021/np400683h

  日期：2013.12.27

  spectroscopic data. The absolute configurations of 1–8 were determined by chemical hydrolysis and modified Mosher’s and Marfey’s methods. All compounds were tested in an anti-HIV activity assay, and compound 1 showed an inhibitory effect on HIV-1 replication by targeting reverse transcriptase. Further study exhibited that 1 could block NNRTIs-resistant strains (HIV-1RT-K103N, HIV-1RT-L100I,K103N, HIV-1RT-K103N

  七个新phenylspirodrimanes，命名stachybotrins d-F（1，3，4），stachybocins E和F（5，6），和stachybosides A和B（7，8），和四个已知化合物（2，9 - 11），从海绵来源的真菌Stachybotrys chartarum MXH-X73中分离得到。它们的结构是通过对光谱数据的详细分析来确定的。1 – 8的绝对构型是通过化学水解以及改良的Mosher法和Marfey法确定的。所有化合物均经过抗HIV活性检测，图1显示了通过靶向逆转录酶对HIV-1复制的抑制作用。进一步的研究表明1可以阻断NNRTIs耐药株（HIV-1 RT-K103N，HIV-1 RT-L100I，K103N，HIV-1 RT-K103N，V108I，HIV-1 RT-K103N，G190A和HIV-1 RT-K103N，P225H）以及EC 50分别为7