D-allo-Thr-L-FDLA | 199729-91-4

• 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: D-allo-Thr-L-FDLA
• 英文别名: D-Thr-L-DLA
• CAS: 199729-91-4
• 化学式: C₁₆H₂₃N₅O₈
• 分子量: 413.387
• InChiKey: QKRPNLULHSNEII-FDLBOYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  210.96
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  D-别苏氨酸 、 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 1.0h， 生成 D-allo-Thr-L-FDLA
  参考文献：
  名称：

  3D NMR 在肽天然产物结构测定中的应用

  摘要：

  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。

  DOI：

  10.1021/acs.joc.5b01486

文献信息

• Octaminomycins A and B, Cyclic Octadepsipeptides Active against <i>Plasmodium falciparum</i>
  作者：Jun-Pil Jang、Toshihiko Nogawa、Yushi Futamura、Takeshi Shimizu、Daisuke Hashizume、Shunji Takahashi、Jae-Hyuk Jang、Jong Seog Ahn、Hiroyuki Osada

  DOI：10.1021/acs.jnatprod.6b00758

  日期：2017.1.27

  octadepsipeptides, octaminomycins A (1) and B (2), were isolated from a microbial metabolite fraction library of Streptomyces sp. RK85-270 based on Natural Products Plot screening. Their structures were elucidated on the basis of HRESIMS, 1D and 2D NMR spectroscopic data, and MS/MS experiments for sequence analysis. The absolute configurations of the constituent amino acid residues were determined by a combination

  两个新的环状十八肽，八氨基霉素A（1）和B（2），是从链霉菌（Streptomyces sp ）的微生物代谢物组分库中分离出来的。RK85-270基于天然产物图筛选。在HRESIMS，1D和2D NMR光谱数据以及用于序列分析的MS / MS实验的基础上阐明了它们的结构。组成氨基酸残基的绝对构型是通过单晶X射线衍射和Marfey方法相结合确定的。值得注意的是，八氨基霉素A（1）和B（2）对氯喹敏感和对氯喹具有抗性的菌株显示出良好的体外抗血浆活性，最高30μM时无细胞毒性。
• Structure and Biosynthesis of Xenoamicins from Entomopathogenic <i>Xenorhabdus</i>
  作者：Qiuqin Zhou、Florian Grundmann、Marcel Kaiser、Matthias Schiell、Sophie Gaudriault、Andreas Batzer、Michael Kurz、Helge B. Bode

  DOI：10.1002/chem.201302481

  日期：2013.12.2

  products from entomopathogenic Xenorhabdus doucetiae DSM17909 and X. mauleonii DSM17908 novel peptides named xenoamicins were identified in addition to the already known antibiotics xenocoumacin and xenorhabdin. Xenoamicins are acylated tridecadepsipeptides consisting of mainly hydrophobic amino acids. The main derivative xenoamicin A (1) was isolated from X. mauleonii DSM17908, and its structure elucidated

  在寻找来自致病性致病性希诺氏杆菌DSM17909和莫氏杆菌X.DSM17908的新型天然产物的过程中，除了已知的抗生素异诺香豆素和异诺哈丁以外，还鉴定了名为异诺霉素的新型肽。Xenoamicins是主要由疏水性氨基酸组成的酰化三聚肽。从莫氏木霉DSM17908中分离了主要衍生物异诺霉素A（1），并通过详细的1 D和2 D NMR实验阐明了其结构。详细的MS实验，也与标记实验相结合，确认了确定的结构，并阐明了其他衍生物的结构。此外，鉴定和分析了xenoamicin生物合成基因簇。诱变证实了X. doucetiae DSM17909及其参与异农霉素的生物合成。先进的Marfey对1的分析表明，氨基酸的绝对构型与从非核糖体肽合成酶XabABCD推导的预测立体化学相符。生物测试显示，抗恶性疟原虫和其他被忽视的热带病的活性为1，但没有抗菌活性。
• Melicopteline A–E, Unusual Cyclopeptide Alkaloids with Antiviral Activity against Influenza A Virus from <i>Melicope pteleifolia</i>
  作者：Ba Wool Lee、Thi Kim Quy Ha、Eun Jin Park、Hyo Moon Cho、Byeol Ryu、Thi Phuong Doan、Hee Ju Lee、Won Keun Oh

  DOI：10.1021/acs.joc.0c02137

  日期：2021.1.15
• 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.
• 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).