| 199729-96-9

• 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
• CAS: 199729-96-9
• 化学式: C₁₆H₂₂N₆O₈
• 分子量: 426.386
• InChiKey: VXOCXBBGNOQLLZ-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  233.82
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  L-天冬酰胺 、 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 1.0h， 生成
  参考文献：
  名称：

  Callyaerins A–F and H, new cytotoxic cyclic peptides from the Indonesian marine sponge Callyspongia aerizusa

  摘要：

  Bioassay guided fractionation of the EtOAc fraction of the sponge Callyspongia aerizusa yielded seven new cytotoxic cyclic peptides callyaerins A-F (1-6) and H (8). Their structures were determined using extensive 1D (H-1, C-13 and DEPT) and 2D (COSY, HMQC, HMBC, TOCSY, and ROESY) NMR and mass spectral (ESI and HRESI-TOF) data. All compounds were cyclic peptides containing ring systems of 5-9 amino acids and side chains of 2-5 amino acids in length. An unusual (Z)-2,3-diaminoacrylic acid unit provided the template for ring closure and afforded the linkage to the peptidic side chain which was always initiated with a proline moiety. All peptides contained three or more proline residues and the remaining residues were predominantly hydrophobic residues with all amino acids present in the L form. Callyaerins A-F (1-6) and H (8) showed biological activity in antibacterial assays and in various cytotoxicity assays employing different tumour cell-lines (L5178Y, HeLa, and PC12). Callyaerins E (5) and H (8) exhibited strong activity against the L5178Y cell line with ED50 values of 0.39 and 0.48 mu M, respectively. On the other hand, callyaerin A (1) showed strong inhibitory properties towards C. albicans. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.012

文献信息

• Ulleungdin, a Lasso Peptide with Cancer Cell Migration Inhibitory Activity Discovered by the Genome Mining Approach
  作者：Sangkeun Son、Mina Jang、Byeongsan Lee、Young-Soo Hong、Sung-Kyun Ko、Jae-Hyuk Jang、Jong Seog Ahn

  DOI：10.1021/acs.jnatprod.8b00449

  日期：2018.10.26

  found biosynthetic genes encoding a new lasso peptide in the genome sequence of a soil bacterium, Streptomyces sp. KCB13F003 isolated from Ulleung Island (a small volcanic island), Korea. The production and purification of the encoded peptide, named ulleungdin, were achieved by optimizing the culture conditions followed by LC-MS-targeted isolation. Structure elucidation was performed by NMR spectroscopic

  基因组序列分析和基因组挖掘工具的进步使人们能够开发尚未开发的微生物天然产物。通过基因组挖掘研究以发现隐秘的天然产物，我们在土壤细菌链霉菌（Streptomyces sp。）的基因组序列中发现了编码新的套索肽的生物合成基因。KCB13F003与韩国Ulleung岛（一个小火山岛）隔离。通过优化培养条件，然后进行LC-MS靶向分离，可以实现编码为ulleungdin的肽的生产和纯化。通过NMR光谱和MS光谱分析以及化学方法（Marfey和GITC衍生化）进行结构阐明，证明ulleungdin是一种具有螺纹结构的新型15-mer II类套索肽。
• Cystomanamides: Structure and Biosynthetic Pathway of a Family of Glycosylated Lipopeptides from Myxobacteria
  作者：Lena Etzbach、Alberto Plaza、Ronald Garcia、Sascha Baumann、Rolf Müller

  DOI：10.1021/ol500779s

  日期：2014.5.2

  Cystomanamides A-D were isolated as novel natural product scaffolds from Cystobacter fuscus MCy9118, and their structures were established by spectroscopic techniques including 2D NMR, LC-SPE-NMR/-MS, and HR-MS. The cystomanamides contain beta-hydroxy amino acids along with 3-amino-9-methyldecanoic acid that is N-glycosylated in cystomanamide C and D. The gene cluster for cystomanamide biosynthesis was identified by gene disruption as PKS/NRPS hybrid incorporating an iso-fatty acid as starter unit and including a reductive amination step at the interface of the PKS and NRPS modules.
• Microseiramide from the freshwater cyanobacterium Microseira sp. UIC 10445
  作者：Shangwen Luo、Aleksej Krunic、George E. Chlipala、Jimmy Orjala

  DOI：10.1016/j.phytol.2015.05.003

  日期：2015.9

  Microseiramide (1), a cyclic heptapeptide, was isolated from a sample of the freshwater cyanobacterium Microseira sp. UIC 10445 collected in a shallow lake in Northern Indiana. Taxonomic identification of UIC 10445 was performed by a combination of morphological and phylogenetic characterization. Phylogenetic analysis revealed that UIC 10445 was a member of the recently described genus Microseira, which is phylogenetically distinct from the morphologically similar genera, Moorea and Lyngbya. The planar structure of microseiramide (1) was determined by extensive 1D and 2D NMR experiments as well as HRESIMS analysis. The absolute configurations of amino acid residues were determined using acid hydrolysis followed by the advanced Marfey's analysis. Microseiramide (1) is the first cyclic peptide reported from a Microseira sp., and the structure of microseiramide (1) is distinct from the previously known metabolites from cyanobacteria of the genera Moorea and Lyngbya. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.