D-Arg-L-FDLA | 199730-17-1

• 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: D-Arg-L-FDLA
• CAS: 199730-17-1
• 化学式: C₁₈H₂₈N₈O₇
• 分子量: 468.47
• InChiKey: CQGGJKHIMZWZRT-MFKMUULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  33.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  D-精氨酸 、 NAlpha-(5-氟-2,4-二硝基苯基)-L-亮氨酰胺 以 丙酮 为溶剂， 生成 D-Arg-L-FDLA
  参考文献：
  名称：

  LC-MS 引导下从氰化放线菌 LHW52806 中分离氰基肽 A–C（具有 β-甲基亮氨酸残基的环脂肽）

  摘要：

  氰基肽 A–C ( 1 – 3 ) 是三种具有不寻常 β-甲基-亮氨酸残基的新环脂肽，是使用 LC-MS 引导策略从Actinoalloteichuscyanogriseus LHW52806 中鉴定出来的。通过 1D/2D NMR、HR-MS/MS 和先进的 Marfey 方法阐明了化合物1 – 3的结构。β-甲基-亮氨酸残基的绝对构型通过 (2 S ,3 R )-β-甲基-亮氨酸的立体选择性生物合成、外消旋至其差向异构体 (2 R ,3 R )-β-甲基-的组合来确定。亮氨酸，以及先进的 Marfey 方法。通过对A.基因组的分析，推导了氰基肽的生物合成途径。蓝鲸LHW52806。化合物3对幽门螺杆菌G27、幽门螺杆菌26695和耻垢分枝杆菌ATCC607表现出抗菌活性，MIC值为32 μg/mL。

  DOI：

  10.1021/acs.jnatprod.3c00127

文献信息

• Argicyclamides A–C Unveil Enzymatic Basis for Guanidine Bis-prenylation
  作者：Chin-Soon Phan、Kenichi Matsuda、Nandani Balloo、Kei Fujita、Toshiyuki Wakimoto、Tatsufumi Okino

  DOI：10.1021/jacs.1c05732

  日期：2021.7.14

  prenylation is an outstanding modification in alkaloid and peptide biosynthesis, but its enzymatic basis has remained elusive. We report the isolation of argicyclamides, a new class of cyanobactins with unique mono- and bis-prenylations on guanidine moieties, from Microcystis aeruginosa NIES-88. The genetic basis of argicyclamide biosynthesis was established by the heterologous expression and in vitro characterization

  胍异戊二烯化是生物碱和肽生物合成中的一种突出修饰，但其酶学基础仍然难以捉摸。我们报告了从铜绿微囊藻NIES-88中分离出的一种新型氰基细菌素，一种在胍基上具有独特的单异戊二烯化和双异戊二烯化的新型氰基环酰胺。argicyclamide 生物合成的遗传基础是通过生物合成酶的异源表达和体外表征建立的，包括 AgcF，一种新的胍异戊二烯基转移酶。这项研究为异戊二烯化胍的生物合成提供了重要的见解，并为肽修饰提供了一个新的工具包。
• Application of 3D NMR for Structure Determination of Peptide Natural Products
  作者：Fan Zhang、Navid Adnani、Emmanuel Vazquez-Rivera、Doug R. Braun、Marco Tonelli、David R. Andes、Tim S. Bugni

  DOI：10.1021/acs.joc.5b01486

  日期：2015.9.4

  in NMR, structure determination is often slow and constitutes a bottleneck in natural products discovery. Removal of this bottleneck would greatly improve the throughput for antibiotic discovery as well as other therapeutic areas. Overall, faster structure methods for structure determination will serve the natural products community in a broad manner. This report describes the first application of

  尽管核磁共振技术取得了进步，但结构测定通常很慢，并且构成了天然产物发现的瓶颈。消除这一瓶颈将大大提高抗生素发现以及其他治疗领域的吞吐量。总体而言，用于结构测定的更快的结构方法将以广泛的方式服务于天然产物界。本报告描述了 3D NMR 首次应用于阐明两种具有新颖结构的微生物产生的肽天然产物。这些方法具有成本效益，并且大大提高了对所提出结构的信心。
• New cytotoxic callipeltins from the Solomon Island marine sponge Asteropus sp.
  作者：Marc Stierhof、Kine Østnes Hansen、Mukesh Sharma、Klaus Feussner、Karolina Subko、Fernando Fernández Díaz-Rullo、Johan Isaksson、Ignacio Pérez-Victoria、David Clarke、Espen Hansen、Marcel Jaspars、Jioji N. Tabudravu

  DOI：10.1016/j.tet.2016.09.016

  日期：2016.11

  Four new callipeltin A derivatives (N–Q) have been isolated from the Solomon Island marine sponge Asteropus sp. Their structures were established by spectroscopic techniques followed by acid hydrolysis and derivatisation of the free amino acids, and subsequent LCMS analysis of the derivatives. The compounds were evaluated for their activity against cancer cell lines A2058 (melanoma), HT-29 (colorectal

  从所罗门岛海洋海绵Asteropus sp。中分离出了四种新的callipeltin A衍生物（N–Q）。通过光谱技术确定其结构，然后进行酸水解和游离氨基酸的衍生化，然后对衍生物进行LCMS分析。评估了化合物对癌细胞系A2058（黑色素瘤），HT-29（结肠直肠腺癌）和MCF-7（乳腺癌）和非恶性MRC-5成纤维细胞的活性。无环愈伤组织P和Q处于非活性状态，而环状愈伤组织N和O对所有暴露的细胞系均表现出明显的细胞毒性，IC 50值低至0.16μM，这证实了环状构型在生物活性中的作用。
• Chlorocatechelins A and B from <i>Streptomyces</i> sp.: New Siderophores Containing Chlorinated Catecholate Groups and an Acylguanidine Structure
  作者：Shinji Kishimoto、Shinichi Nishimura、Akira Hattori、Masafumi Tsujimoto、Masaki Hatano、Masayuki Igarashi、Hideaki Kakeya

  DOI：10.1021/ol502964s

  日期：2014.12.5

  Two novel siderophores, chlorocatechelins A and B, were isolated from a culture broth of Streptomyces sp. Their structures were determined by spectroscopic analysis and degradation study. They contain chloro-substituted catecholate that has not been reported in natural products, whereas this group was conjugated to guanidine to form acylguanidine in chlorocatechelin A. This acylguanidine decomposed in weakly acidic solutions to furnish a less potent siderophore chlorocatechelin B. Chemical and biological insights into acylguanidine are also discussed.
• Stictamides A−C, MMP12 Inhibitors Containing 4-Amino-3-hydroxy-5-phenylpentanoic Acid Subunits
  作者：Zhibin Liang、Analia Sorribas、Florian J. Sulzmaier、Jorge I. Jiménez、Xin Wang、Thomas Sauvage、Wesley Y. Yoshida、Guangyi Wang、Joe W. Ramos、Philip G. Williams

  DOI：10.1021/jo200241h

  日期：2011.5.20

  An extensive study of the secondary metabolites produced by a new Sticta sp. of lichen has led to the isolation of three new compounds containing the 4-amino-3-hydroxy-5-phenylpentanoic acid residue (Ahppa). The structures of stictamides A-C (1-3) were assigned by 2D NMR spectroscopic and chemical methods. Due to extensive epimerization of the Ahppa residue observed after acid hydrolysis, the configuration of this unit was deduced through conversion of 1 to an appropriate derivative and application of our recently developed statine NMR database. Evaluation of stictamide A against a panel of disease-relevant proteases showed that it inhibited MMP12 at 2.3 mu M and significantly reduced invasion in the human glioma cell line U87MG. Docking studies suggest that stictamide A inhibits MMP12 by a non-zinc-binding mechanism.