L-FDAA-L-ornitine | 194736-46-4

• 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: L-FDAA-L-ornitine
• 英文别名: FDAA-L-Orn
• CAS: 194736-46-4
• 化学式: C₁₄H₂₀N₆O₇
• 分子量: 384.349
• InChiKey: ZCZCXYAVNHRTKC-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  27.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  acremonpeptide A 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 水 、 氢碘酸 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 L-FDAA-L-ornitine 、 (S)-2-amino-5-((5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)amino)pentanoic acid 、 DAA-(Nδ-DAA)-Orn
  参考文献：
  名称：

  天然的含异羟肟酸酯的铁载体Acremonpeptides AD和来自海洋衍生的Apermonium persicinum SCSIO 115的Acremonpeptide D的铝配合物。

  摘要：

  从海洋真菌桃圆孢菌SCSIO 115中获得了四个新的含异羟肟酸酯的天然产物环肽，称为顶肽AD（1-4）和Al（III）-re肽D（5）。 HRMS以及1D和2D NMR数据集的基础。此外，氨基酸的绝对构型是使用Marfey法确定的。化合物1-5均具有三个2-氨基-5-（N-羟基乙酰胺基）戊酸（N5-羟基-N5-乙酰基-1-鸟氨酸）金属离子螯合部分。除了发现和阐明结构外，体外生物测定还显示出顶角肽A（1），B（2）和Al（III）-re肽D（5）作为单纯疱疹病毒1的中度抗病毒剂，其EC50值为16、8.7，和14μM。

  DOI：

  10.1021/acs.jnatprod.9b00545

文献信息

• 5-OHKF and NorKA, Depsipeptides from a Hawaiian Collection of <i>Bryopsis pennata</i>: Binding Properties for NorKA to the Human Neuropeptide Y Y₁ Receptor
  作者：Jiangtao Gao、Catherina Caballero-George、Bin Wang、Karumanchi V. Rao、Abbas Gholipour Shilabin、Mark T. Hamann

  DOI：10.1021/np900287e

  日期：2009.12.28

  Two new cyclic depsipeptides, 5-OHKF (1) and norKA (2), together with the known congeners kahalalide F (3) and isokahalalide F ((4S)- methylhexanoic kahalalide F) (4) were isolated from the green alga Bryopsis pennata. The structures of the new compounds were established on the basis of extensive 1D and 2D NMR spectroscopic analysis and mass spectrometric (ESIMS) data. The absolute configuration of

  从绿藻Bryopsis中分离出两种新的环状缩肽 5-OHKF ( 1 ) 和 norKA ( 2 )，以及已知的同源物 kahalalide F ( 3 ) 和异甘氨酸酯 F ((4 S )-methylhexanoic kahalalide F) ( 4 )彭纳塔。新化合物的结构是在广泛的 1D 和 2D NMR 光谱分析和质谱 (ESIMS) 数据的基础上确定的。5-OHKF ( 1 ) 和norKA ( 2 )的每个氨基酸的绝对构型通过化学降解和Marfey 分析确定。还报道了这两种化合物的生物活性。
• Cyclic Tripeptides from the Halotolerant Fungus <i>Aspergillus sclerotiorum</i> PT06-1
  作者：Jinkai Zheng、Zhihong Xu、Yi Wang、Kui Hong、Peipei Liu、Weiming Zhu

  DOI：10.1021/np100198h

  日期：2010.6.25

  Eleven new aspochracin-type cyclic tripeptides, sclerotiotides A-K (1-11), together with three known compounds, JBIR-15 (12), aspochracin (13), and penicillic acid, were isolated from the ethyl acetate extract of the fermentation broth of the halotolerant Aspergillus sclerotiorum PT06-1 in a hypersaline nutrient-rich medium. Their structures were elucidated by spectroscopic analysis and chemical methods. Chemical transformations of 12 and 13 proved that sclerotiotides D K (4-11) were artifacts probably formed during the fermentation or subsequent isolation steps. All 13 cyclic tripeptides have been evaluated for their antimicrobial and cytotoxic effects. Only sclerotiotides A (1), 13 (2), F (6), and I (9) and JBIR-15 (12) showed selective antifungal activity against Candida albicans with MIC values of 7.5, 3.8, 30, 6.7, and 30 mu M, respectively.
• Structure and Biosynthetic Assembly of Cupriachelin, a Photoreactive Siderophore from the Bioplastic Producer Cupriavidus necator H16
  作者：Martin F. Kreutzer、Hirokazu Kage、Markus Nett

  DOI：10.1021/ja300620z

  日期：2012.3.21

  The bacterium Cupriavidus necator H16 produces a family of linear lipopeptides when grown under low iron conditions. The structural composition of these molecules, exemplified by the main metabolite cupriachelin, is reminiscent of siderophores that are excreted by marine bacteria. Comparable to marine siderophores, the ferric form of cupriachelin exhibits photoreactive properties. Exposure to UV light induces an oxidation of its peptidic backbone and a concomitant reduction of the coordinated Fe(III). Here, we report the genomics-inspired isolation and structural characterization of cupriachelin as well as its encoding gene cluster, which was identified by insertional mutagenesis. Based upon the functional characterization of adenylation domain specificity, a model for cupriachelin biosynthesis is proposed.
• Nicrophorusamides A and B, Antibacterial Chlorinated Cyclic Peptides from a Gut Bacterium of the Carrion Beetle <i>Nicrophorus concolor</i>
  作者：Yern-Hyerk Shin、Suhyun Bae、Jaehoon Sim、Joonseong Hur、Shin-Il Jo、Jongheon Shin、Young-Ger Suh、Ki-Bong Oh、Dong-Chan Oh

  DOI：10.1021/acs.jnatprod.7b00506

  日期：2017.11.22

  Nicrophorusamides A and B (1 and 2) were discovered from a rare actinomycete, Microbacterium sp., which was isolated from the gut of the carrion beetle Nicrophorus concolor. The structures of the nicrophorusamides were established as new chlorinated cyclic hexapeptides bearing uncommon amino acid units mainly based on 1D and 2D NMR spectroscopic analysis. The absolute configurations of the amino acid residues S-chloro-L-tryptophan, D-threo-beta-hydroxyasparagine/D-asparagine, L-omithine, L-allo-isoleucine, D-leucine, and D-valine were determined using Marfey's method and chemical derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate followed by LC/MS analysis. Nicrophorusamide A (1) showed antibacterial activity against several Gram-positive bacteria.