N-(5-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-2,4-dinitrophenyl)-N-methyl-L-alanine | 847925-49-9

• 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-alanine
• 英文别名: L-DLA-L-Nma
• CAS: 847925-49-9
• 化学式: C₁₆H₂₃N₅O₇
• 分子量: 397.388
• InChiKey: SQUUQTAJXNASFJ-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-丙氨酸 、 NAlpha-(5-氟-2,4-二硝基苯基)-L-亮氨酰胺 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 N-(5-(((S)-1-amino-4-methyl-1-oxopentan-2-yl)amino)-2,4-dinitrophenyl)-N-methyl-L-alanine
  参考文献：
  名称：

  Pithohirolide，一种来自真菌 Pithomyces chartarum 的抗菌四肽

  摘要：

  Pithohirolide ( 1 ) 是一种新的缩酚肽，是从子囊菌真菌Pithomyces chartarum TAMA 581 中分离出来的。1的平面结构在 NMR 和 MS 分析的基础上阐明，绝对构型由高级 Marfey 分析确定，手性相HPLC分析和降解产物的合成。化合物1具有环状结构，包括( S )-2-羟基-3-苯基丙酸、( S )-3-羟基-3-苯基丙酸、( S )-2-羟基异戊酸和N-甲基-1-丙氨酸，通过三个酯键和一个酰胺键连接。化合物1在 MIC 3.1 μg ml -1 时表现出对金黄色葡萄球菌和酿酒酵母的抗菌活性。

  DOI：

  10.1038/s41429-021-00423-4

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。
• Stellettapeptins A and B, HIV-inhibitory cyclic depsipeptides from the marine sponge Stelletta sp.
  作者：Hee Jae Shin、Mohammad A. Rashid、Laura K. Cartner、Heidi R. Bokesch、Jennifer A. Wilson、James B. McMahon、Kirk R. Gustafson

  DOI：10.1016/j.tetlet.2015.05.058

  日期：2015.7

  Two new HIV-inhibitory depsipeptides, stellettapeptins A (1) and B (2), were isolated from an extract of the marine sponge Stelletta sp., collected from northwestern Australia. Structures of these cyclic nonribosomal peptides were elucidated on the basis of extensive NMR data analysis, and chemical degradation and derivatization studies. Stellettapeptins contain numerous nonproteinogenic amino acid

  从澳大利亚西北部收集的海洋海绵Stelletta sp。的提取物中分离出两种新的HIV抑制性十肽肽stellettapeptins A（1）和B（2）。这些环状非核糖体肽的结构在广泛的NMR数据分析，化学降解和衍生化研究的基础上得到阐明。Stellettapeptins包含许多非蛋白质氨基酸残基，它们是第一个据报道包含3-羟基-6,8-二甲基非-4-（Z）-烯酸部分的肽。化合物1和2可以有效抑制HIV 50 RF与EC 50对人T淋巴细胞的感染 值分别为23和27 nM。
• Jubanines F–J, cyclopeptide alkaloids from the roots of Ziziphus jujuba
  作者：Kyo Bin Kang、Gao Ming、Geum Jin Kim、Thi-Kim-Quy Ha、Hyukjae Choi、Won Keun Oh、Sang Hyun Sung

  DOI：10.1016/j.phytochem.2015.09.001

  日期：2015.11

  Five Ib-type cyclopeptide alkaloids, jubanines F-J (1-5), and three known compounds, nummularine B (6), daechuine-S3 (7), and mucronine K (8) were isolated from the roots of Ziziphus jujuba. Their structures were fully characterized by spectroscopic analyses in combination with chemical derivatization. Compounds 1-3, and 6 were evaluated for their antiviral activity against the porcine epidemic diarrhea virus (PEDV). Compounds 2, 3, and 6 showed potent inhibitory effects on PEDV replication. (C) 2015 Elsevier Ltd. All rights reserved.
• Cyclic Depsipeptides, Grassypeptolides D and E and Ibu-epidemethoxylyngbyastatin 3, from a Red Sea <i>Leptolyngbya</i> Cyanobacterium
  作者：Christopher C. Thornburg、Muralidhara Thimmaiah、Lamiaa A. Shaala、Andrew M. Hau、Jay M. Malmo、Jane E. Ishmael、Diaa T. A. Youssef、Kerry L. McPhail

  DOI：10.1021/np200270d

  日期：2011.8.26

  Two new grassypeptolides and a lyngbyastatin analogue, together with the known dolastatin 12, have been isolated from field collections and laboratory cultures of the marine cyanobacterium Leptolyngbya sp. collected from the SS Thistlegorm shipwreck in the Red Sea. The overall stereostructures of grassypeptolides D (1) and E (2) and Ibu-epidemethoxylyngbyastatin 3 (3) were determined by a combination of 1D and 2D NMR experiments, MS analysis, Marfey's methodology, and HPLC-MS. Compounds 1 and 2 contain 2-methyl-3-aminobutyric acid and 2-aminobutyric acid, while biosynthetically distinct 3 contains 3-amino-2-methylhexanoic acid and the beta-keto amino acid 4-amino-2,2-dimethyl-3-oxopentanoic acid (Ibu). Grassypeptolides D (1) and E (2) showed significant cytotoxicity to HeLa (IC50 = 335 and 192 nM, respectively) and mouse neuro-2a blastoma cells (IC50 = 599 and 407 nM, respectively), in contrast to Ibu-epidemethoxylyngbyastatin 3 (neuro-2a cells, IC50 > 10 mu M) and dolastatin 12 (neuro-2a cells, IC50 > 1 mu M).