(5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-L-arginine | 128424-99-7

• 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-arginine
• CAS: 128424-99-7
• 化学式: C₁₅H₂₂N₈O₇
• 分子量: 426.389
• InChiKey: YVBJEIXKNMKFNU-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.08
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  252.63
• 氢给体数：
  7.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  L-精氨酸盐酸盐 、 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 (5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-L-arginine
  参考文献：
  名称：

  由鲁克氏耶尔森菌 YRB 产生的 Ruckerbactin 是由坎贝氏弧菌 DS40M4 产生的铁载体 Trivanchrobactin 的非对映异构体

  摘要：

  革兰氏阴性菌鲁氏耶尔森氏菌是鲑鱼肠道红口病的病原体。 Y. ruckeri YRB 的基因组包含一个生物合成基因簇，编码儿茶酚铁载体的生物合成，这些铁载体与已知的 vanchrobactin 类铁载体 (DHB D Arg L Ser) (DHB D Arg L Ser) (1–3)呈非对映异构体。 Ruckerbactin ( 1 )由Y. ruckeri YRB产生，被发现是由L-精氨酸和2,3-二羟基苯甲酸组成的直链三-L-丝氨酸酯(DHB L Arg L Ser) 3 。双儿茶酚 (DHB L Arg L Ser) 2 ( 2 ) 和单儿茶酚 DHB L Arg L Ser ( 3 ) 化合物也被分离和表征。未检测到 Ruckerbactin 的大环内酯。 Ruckerbactin 中L Arg 的存在使其成为 trivanchrobactin 与D Arg 的非对映异构体。 Fe(III)-ruckerbactin

  DOI：

  10.1021/acs.jnatprod.1c01047

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。
• Namalides B and C and Spumigins K–N from the Cultured Freshwater Cyanobacterium <i>Sphaerospermopsis torques-reginae</i>
  作者：Miriam Sanz、Roberto Kopke Salinas、Ernani Pinto

  DOI：10.1021/acs.jnatprod.7b00370

  日期：2017.9.22

  namalides B (1) and C (2), the first analogues of this anabaenopeptide-like metabolite to be described. Four other related peptides (3–6), termed spumigins K–N, were also identified. Planar structures and absolute configurations for 1, 2, and 3a–6a were deduced by a combination of 2D NMR, HRMS analysis, and Marfey’s methodology. Spumigins K–N (3–6) are the first examples of spumigins containing a 2-hyd

  来自巴西北部的陆地蓝藻Sphaerospermopsis扭矩-reginae ITEP-024的化学研究提供了纳马利德B（1）和C（2），这是拟被描述的阿那贝肽类代谢物的第一个类似物。还鉴定了其他四个相关肽（3 – 6），称为spumigins K–N。平面结构和绝对构型1，2，和图3a -图6a是由2D NMR，HRMS分析，和的Marfey的方法的组合推导。Spunigins K–N（3 – 6）是在N端位置含有2-羟基-4-（4-羟基苯基）丁酸（Hhpba）的Spumigins的第一个例子。化合物1和2抑制羧肽酶A的IC 50值分别为0.75和2.0μM。
• Chiral derivatization-enabled discrimination and on-tissue detection of proteinogenic amino acids by ion mobility mass spectrometry
  作者：Chengyi Xie、Yanyan Chen、Xiaoxiao Wang、Yuanyuan Song、Yuting Shen、Xin Diao、Lin Zhu、Jianing Wang、Zongwei Cai

  DOI：10.1039/d2sc03604e

  日期：——

  biological samples was proven in matrix-assisted laser desorption/ionization (MALDI) TIMS mass spectrometry imaging (MSI) as well by directly depositing 19 pairs of chiral AAs on a tissue slide following on-tissue derivatization. In addition, endogenous chiral amino acids were also detected and distinguished. The developed methods show compelling application prospects in biomarker discovery and biological

  自从发现内源性D -AAs 作为几种代谢紊乱的潜在生物标志物以来，手性氨基酸 (AAs) 在生物体中的重要性已得到广泛认可。离子迁移谱-质谱法（IMS-MS）的手性分析具有速度快、灵敏度高等优点，但仍处于起步阶段。此处，N α -(2,4-二硝基-5-氟苯基)- L-丙氨酰胺 (FDAA) 衍生化与俘获离子淌度质谱 (TIMS-MS) 相结合，用于手性 AA 分析。我们首次展示了在单个固定条件 TIMS-MS 运行中同时分离 19 对手性蛋白氨基酸。通过直接注入 TIMS-MS 提出了这种方法对小鼠大脑提取物的实用性。基质辅助激光解吸/电离 (MALDI) TIMS 质谱成像 (MSI) 以及在组织衍生化后将 19 对手性 AA 直接沉积在组织载玻片上证明了复杂生物样品的强大分离能力。此外，还检测并区分了内源性手性氨基酸。所开发的方法在生物标志物发现和生物学研究中显示出引人注目的应用前景。
• Protease Inhibitors from <i>Microcystis aeruginosa</i> Bloom Material Collected from the Dalton Reservoir, Israel
  作者：Simi Adiv、Shmuel Carmeli

  DOI：10.1021/np4006844

  日期：2013.12.27

  Nine new metabolites, aeruginosins DA495A (1), DA511 (2), DA642A (3), DA642B (4), DA688 (5), DA722 (6), and DA495B (7), microguanidine DA368 (8), and anabaenopeptin DA850 (9), were isolated along with the known micropeptins MZ924, MZ939A, and MZ1019, cyanopeptolins S and SS, microcin SF608, and aeruginazoles DA1497, DA1304, and DA1274 from bloom material of the cyanobacterium Microcystis aeruginosa collected from the Dalton reservoir, Israel, in October 2007. Their structures were elucidated by a combination of various spectroscopic techniques, primarily NMR and MS, while the absolute configurations of the asymmetric centers were determined by Marfey's and chiral-phase HPLC methods. Two of the new aeruginosins, DA511 (1) and DA495A (2), contain a new Choi isomer, (2S,3aS,6S,7aS)-Choi. The structure elucidation and biological activities of the new metabolites are described.
• Eight micropeptins from a Microcystis spp. bloom collected from a fishpond near Kibbutz Lehavot HaBashan, Israel
  作者：Margarita Vegman、Shmuel Carmeli

  DOI：10.1016/j.tet.2013.09.054

  日期：2013.11

  Eight new micropeptin-type cyclic depsipeptides, micropeptins LH920, LH1021, LH1048, LH1062, LH911A, LH911B, LH911C, and LH925, along with five known micropeptins, three known anabaenopeptins and two known microcystins (LR and RR), were isolated from a water bloom biomass of Microcystis spp. assembly that was collected from a fishpond near Kibbutz Lehavot HaBashan, Israel. The structures of the pure compounds were elucidated using 1D and 2D NMR techniques, as well as high-resolution mass spectrometry. The stereochemistry of the new natural products was determined using Marfey's method for amino acids. The inhibitory activity of the compounds was determined for the serine proteases, trypsin, and chymotrypsin. (C) 2013 Elsevier Ltd. All rights reserved.