N-(5-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-2,4-dinitrophenyl)-N-methyl-L-valine | 847926-85-6

• 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: N-(5-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-2,4-dinitrophenyl)-N-methyl-L-valine
• 英文别名: L-DLA-N-Me-L-Val；L-FDLA-L-MeVal
• CAS: 847926-85-6
• 化学式: C₁₈H₂₇N₅O₇
• 分子量: 425.442
• InChiKey: ZLVOLYISOUFQDH-LRDDRELGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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-L-缬氨酸 、 NAlpha-(5-氟-2,4-二硝基苯基)-L-亮氨酰胺 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 0.05h， 生成 N-(5-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-2,4-dinitrophenyl)-N-methyl-L-valine
  参考文献：
  名称：

  来自东加勒比海蓝细菌 Lyngbya majuscula 收集的卤代脂肪酸酰胺和环缩肽†

  摘要：

  东加勒比收集的Lyngbya majuscula的亲脂性提取物产生了两种新的卤代脂肪酸酰胺，手榴弹胺 B ( 1 ) 和 C ( 2 )，以及两种新的缩肽，依曲酰胺 A ( 3 ) 和 B ( 4 )，以及已知的化合物八氯环素和脱乙酰八氯环素。最近报道的缩酚肽 carriebowmide ( 5 ) 也存在于提取物中，并作为其砜类人工制品被分离 ( 6 )。化合物1 - 4通过光谱方法鉴定。3 , 4 , 6氨基酸残基的构型通过酸水解产物的非对映异构衍生物的 LC-MS 分析（高级 Marfey 方法）确定。基于6的构型分析，与真正的carriebowmide ( 5 )直接比较，提出了对5的微小结构修正。化合物1和2对甜菜夜蛾（Spodoptera exigua）显示出边际活性。化合物1 - 4和6进行了评估在人胚胎肾（HEK293）细胞一般小区毒性。只有依曲酰胺 B ( 4 ) 显示出显着的细胞毒性，IC

  DOI：

  10.1021/np900173d

文献信息

• Urumamide, a novel chymotrypsin inhibitor with a β-amino acid from a marine cyanobacterium Okeania sp.
  作者：Yuki Kanamori、Arihiro Iwasaki、Shinpei Sumimoto、Kiyotake Suenaga

  DOI：10.1016/j.tetlet.2016.08.012

  日期：2016.9

  Urumamide, a novel cyclic depsipeptide that contains a β-amino acid, was isolated from a marine cyanobacterium Okeania sp. Its gross structure was determined by spectroscopic analyses, and the absolute configuration was established based on Marfey’s analyses and chiral HPLC analyses of hydrolysis products. Biologically, urumamide inhibited the growth of human cancer cells. In addition, urumamide inhibited

  从海洋蓝藻Okeania sp。分离出一种新型的环状β肽Urumamide。通过光谱分析确定其总体结构，并基于Marfey分析和水解产物的手性HPLC分析建立绝对构型。从生物学上说，尿嘧啶抑制人类癌细胞的生长。此外，尿嘧啶可抑制胰凝乳蛋白酶。
• Anti-MRSA actinomycins D1-D4 from the marine sponge-associated Streptomyces sp. LHW52447
  作者：Wei-Hua Jiao、Wei Yuan、Zhi-Yong Li、Jing Li、Lei Li、Jia-Bao Sun、Yu-Han Gui、Jie Wang、Bo-Ping Ye、Hou-Wen Lin

  DOI：10.1016/j.tet.2018.08.023

  日期：2018.10

  Actinomycins D1−D4 (1–4), four new D-type actinomycin analogues, were isolated from the fermentation broth of a strain of marine sponge-associated Streptomyces sp. LHW52447, together with actinomycin D (5). The structures of 1−4 were determined by a combination analysis of HRMS and NMR spectroscopic methods, and their absolute configurations of amino acids were determined by Marfey's analysis. Actinomycins

  放线菌素Def=https://www.molaid.com/MS_40566 target="_blank">放线菌素d 1 -D 4（1 - 4），四个新的d型放线菌素类似物，是从海洋海绵相关的菌株的发酵肉汤中分离链霉菌属。LHW52447，连同放线菌素D（5）。的结构1 - 4通过HRMS和NMR光谱法的组合分析来确定，和它们的氨基酸的绝对构型通过的Marfey的分析来确定。放线菌素D 1（1）和D 2（2）是前两种天然存在的放线菌素，它们在中央苯恶嗪酮发色团中掺入了恶唑单元。既1和2对三个菌株致病耐甲氧西林的显示更有效的抗菌活性的金黄色葡萄球菌（MRSA）具有0.125-0.25微克/毫升的比的MIC值3-5与0.5-1.0 MIC值微克/毫升，这提示通过掺入额外的恶唑单元可以增强抗MRSA的活性。另外，对WI-38人二倍体肺成纤维细胞的细胞毒性评价表明，恶唑单元的掺入可以降低放线菌素对人正常细胞的细胞毒性。
• Odookeanynes A and B, Acetylene-Containing Lipopeptides from an <i>Okeania</i> sp. Marine Cyanobacterium
  作者：Aki Yamano、Yuka Asato、Noriyuki Natsume、Arihiro Iwasaki、Kiyotake Suenaga、Toshiaki Teruya

  DOI：10.1021/acs.jnatprod.1c00915

  日期：2022.1.28
• Coculture of a Pathogenic Actinomycete and Animal Cells To Produce Nocarjamide, a Cyclic Nonapeptide with Wnt Signal-Activating Effect
  作者：Yasumasa Hara、Midori A. Arai、Kazufumi Toume、Hyuma Masu、Tomoyuki Sato、Katsuko Komatsu、Takashi Yaguchi、Masami Ishibashi

  DOI：10.1021/acs.orglett.8b02522

  日期：2018.9.21

  A coculture method with a pathogenic actinomycete of the genus Nocardia and an animal cell line was designed to reconstruct and emulate the initial infection state, and a new cyclic nonapeptide, named nocarjamide (1), was obtained by coculture of Nocardia tenerifensis IFM 10554(T) and the mouse macrophage-like cell line J774.1 in a modified Czapek-Dox medium. Nocarjamide (1) exhibited Wnt signal-activating effects.
• Biseokeaniamides A, B, and C, Sterol <i>O</i>-Acyltransferase Inhibitors from an <i>Okeania</i> sp. Marine Cyanobacterium
  作者：Arihiro Iwasaki、Takato Tadenuma、Shimpei Sumimoto、Taichi Ohshiro、Kaori Ozaki、Keisuke Kobayashi、Toshiaki Teruya、Hiroshi Tomoda、Kiyotake Suenaga

  DOI：10.1021/acs.jnatprod.7b00137

  日期：2017.4.28

  Biseokeaniamides A, B, and C (1-3), structurally novel sterol O-acyltransferase (SOAT) inhibitors; were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Biseokeaniamide B (2) exhibited moderate cytotoxicity against human HeLa cancer cells, and compounds 1-3 inhibited both SOAT1 and SOAT2, not only at an enzyme level but also at a cellular level. Biseokeaniamides (1-3) are the first linear lipopeptides that have been shown to exhibit SOAT-inhibitory activity.