(5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-D-lysine | 194852-55-6

• 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-lysine
• CAS: 194852-55-6
• 化学式: C₁₅H₂₂N₆O₇
• 分子量: 398.376
• InChiKey: IPNKTVIENUIRHO-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  28.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  216.75
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  D-赖氨酸 、 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 (5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-D-lysine
  参考文献：
  名称：

  Protease Inhibitors from a Water Bloom of the Cyanobacterium Microcystis aeruginosa

  摘要：

  Bioassay-guided fractionation of the polar extract of a Microcystis aeruginosa water bloom biomass yielded 10 micropeptins and one anabaenopeptin. Eight of the micropeptins, micropeptins HU1069 (1), HU989 (2), HU1021 (3), HU1041 (4), HU975 (5), HU895A (6), HU909 (7), and HU895B (8), are new, while two, micropeptins 478-A (10) and 478-B (11), were previously isolated from a bloom of M. aeruginosa from Japan. The new anabaenopeptin HU892 (9) belongs to the relatively rare subgroup, presenting an aliphatic amino acid at the carboxylic end of the peptide and N-methylhomoaromatic amino acid at the second position. The structures of the compounds were determined by ID and 2D NMR techniques and mass spectrometric data. The isolated micropeptins inhibited trypsin with IC50'S that varied between 0.7 and 5.2 mu M and unexpectedly inhibited chymotrypsin with IC50's that varied between 2.8 and 72.0 mu M. The SAR of these micropeptins is discussed.

  DOI：

  10.1021/np900340t

文献信息

• 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 novel serine proteases inhibitors from a water bloom of the cyanobacterium Microcystis sp.
  作者：Ella Zafrir-Ilan、Shmuel Carmeli

  DOI：10.1016/j.tet.2010.09.067

  日期：2010.11

  Eight new secondary metabolites micropeptin MM836 (1) micropeptin MM850 (2) micropeptin MM916 (3) micropeptin MM932 (4) micropeptin MM978 (5) anabaenopeptin MM823 (6) anabaenopeptin MM850 (7) and anabaenopeptin MM913 (8) as well as the known anabaenopeptin B (9) were isolated from the hydrophilic extract of the cyanobacterium Microcystis sp that was collected from a fishpond in Kibbutz Ma agan Michael Israel in September 2006 The structure of the pure natural products was established by spectroscopic methods including 1D and 2D NMR, UV and MS techniques The absolute configuration of the chiral centers of the compounds was determined using Marfey s method The inhibitory activity of the compounds was determined against the serine proteases trypsin chymotrypsin thrombin and elastase (C) 2010 Elsevier Ltd All rights reserved