L-cysteine-FDAA | 1122590-61-7

• 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-cysteine-FDAA
• CAS: 1122590-61-7
• 化学式: C₁₂H₁₅N₅O₇S
• 分子量: 373.346
• InChiKey: LUROWSPKKUDQLD-XNCJUZBTSA-N

物化性质

• 沸点：
  749.7±60.0 °C(predicted)
• 密度：
  1.635±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  190.73
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  (2R)-2-[[2-(3-hydroxyquinolin-2-yl)-1,3-oxazole-4-carbonyl]amino]-3-sulanylpropanoic acid 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 甲酸 、 双氧水 、 盐酸 、 水 作用下， 反应 20.0h， 生成 L-cysteine-FDAA
  参考文献：
  名称：

  从海洋衍生的放线菌链霉菌cyaneofuscatus M-157的培养物中获得的新的3-羟基喹啉酸衍生物。

  摘要：

  海洋衍生的放线菌氰基链霉菌M-157的培养物中生物活性提取物的分级分离导致已知的3-羟基喹二酸（4），其酰胺（5）和三个含有不同氨基的新衍生物（1⁻3）的分离。酸残基。新分子（1⁻3）的结构，包括其绝对构型，是通过对其ESI-TOF MS和一维（1D）和二维（2D）NMR光谱进行分析并对其进行高级Marfey分析来确定的水解产物。化合物3在溶液中自发二聚，得到二硫键衍生物6。不幸的是，分离出的新化合物均未证实细菌提取物中具有抗微生物活性，也许表明这种抗菌活性可能是由于提取物中存在痕量的较大的生物活性3-羟基喹啉酸衍生物，化合物1⁻3是它们的生物合成前体。细胞毒性试验证实，化合物5和1的IC50值为中度和弱，分别为15.6和51.5 µM。

  DOI：

  10.3390/md16100371

文献信息

• C₃ and 2D C₃ Marfey’s Methods for Amino Acid Analysis in Natural Products
  作者：Soumini Vijayasarathy、Pritesh Prasad、Leith J. Fremlin、Ranjala Ratnayake、Angela A. Salim、Zeinab Khalil、Robert J. Capon

  DOI：10.1021/acs.jnatprod.5b01125

  日期：2016.2.26

  Marfey’s method, including an ability to resolve all Ile isomers, against an array of amino acids commonly encountered in natural products and by comparison to an existing Marfey’s method. We also describe an innovative 2D C3 Marfey’s method as an analytical approach for determining the regiochemistry of enantiomeric amino acid residues in natural products. The C3 and 2D C3 Marfey’s methods represent

  我们验证了C 3 Marfey方法的改进的分辨率和灵敏度，包括针对天然产物中常见的一系列氨基酸并通过与现有Marfey方法进行比较而解决所有Ile异构体的能力。我们还描述了一种创新的二维C 3 Marfey方法，作为一种确定天然产物中对映体氨基酸残基的区域化学的分析方法。C 3和2 D C 3 Marfey的方法代表了宝贵的工具，可用于探测和定义天然产物中可水解获得的氨基酸残基的立体复杂性。
• Frenolicins C–G, Pyranonaphthoquinones from <i>Streptomyces</i> sp. RM-4-15
  作者：Xiachang Wang、Khaled A. Shaaban、Sherif I. Elshahawi、Larissa V. Ponomareva、Manjula Sunkara、Yinan Zhang、Gregory C. Copley、James C. Hower、Andrew J. Morris、Madan K. Kharel、Jon S. Thorson

  DOI：10.1021/np400231r

  日期：2013.8.23

  databases suggested Streptomyces sp. RM-4-15 to produce unique metabolites. Four new pyranonaphthoquinones, frenolicins C–F (1–4), along with three known analogues, frenolicin (6), frenolicin B (7), and UCF76-A (8), were isolated from the fermentation of this strain. An additional new analogue, frenolicin G (5), along with two known compounds, deoxyfrenolicin (9) and UCF 13 (10), were isolated from the fermentation

  选择阿巴拉契亚活跃的煤火点来分离属于放线菌类的细菌菌株。从分离提取物到天然产物数据库的高分辨率电喷雾电离质谱 (HRESIMS) 和紫外 (UV) 吸收谱的比较表明链霉菌属。RM-4-15 产生独特的代谢物。从该菌株的发酵中分离出四种新的吡喃萘醌类化合物富伦菌素 C–F ( 1 – 4 ) 以及三种已知的类似物富伦菌素 ( 6 )、富伦菌素 B ( 7 ) 和 UCF76-A ( 8 )。另一种新类似物富伦菌素 G ( 5 ) 以及两种已知化合物脱氧富伦菌素 (9 ) 和 UCF 13 ( 10 )，是从提供 18mg/L 氯化钪的发酵中分离出来的，第一个例子，据我们所知，其中氯化钪补充导致新细菌次级代谢产物的确认产生。结构1 - 5分别鉴定光谱分析和化学改性的基础上。而富伦霉素是最适合他们的抗球虫活性已知的，目前的研究显示化合物6 - 9显示出对人肺癌细胞系（A549）中等细胞毒性，并由此延伸，用于这个特权支架抗癌SAR。
• Epidithiodiketopiperazine Biosynthesis: A Four-Enzyme Cascade Converts Glutathione Conjugates into Transannular Disulfide Bridges
  作者：Daniel H. Scharf、Pranatchareeya Chankhamjon、Kirstin Scherlach、Thorsten Heinekamp、Karsten Willing、Axel A. Brakhage、Christian Hertweck

  DOI：10.1002/anie.201305059

  日期：2013.10.11

  Aspergillus fumigatus and successful in vitro conversion of the bisglutathione adduct into an intact epidithiodiketopiperazine by a four‐enzyme cascade (including glutamyltransferase GliK and dipeptidase GliJ) revealed an outstanding adaptation of a primary metabolic pathway into natural product biosynthesis that is widespread in fungi.

  酶四重峰：烟曲霉中胶质毒素途径的第一个含硫中间体的分离，以及通过四酶级联反应（包括谷氨酰转移酶GliK和二肽酶GliJ）成功地将双谷胱甘肽加合物成功地体外转化为完整的表二硫代二酮哌嗪真菌中广泛存在的天然产物生物合成的主要代谢途径。
• A unique indolizinium alkaloid streptopertusacin A and bioactive bafilomycins from marine-derived Streptomyces sp. HZP-2216E
  作者：Xiufang Zhang、Lu Chen、Weiyun Chai、Xiao-Yuan Lian、Zhizhen Zhang

  DOI：10.1016/j.phytochem.2017.09.010

  日期：2017.12

  Streptopertusacin A, a unique indolizinium alkaloid existing as a zwitterion, and six bafilomycins including two previously undescribed ones of 21,22-en-bafilomycin D and 21,22-en-9-hydroxybafilomycin D were isolated from a culture of the seaweed-derived Streptomyces sp. HZP-2216E. Structures of these isolated compounds were determined based on extensive NMR spectroscopic analyses, HRESIMS and MS-MS data. The stereochemical assignments were achieved by NOE information, chemical degradation, Marfey's method, and electronic circular dichroism (ECD) calculation. Streptopertusacin A is the first example of this type of indolizinium alkaloid from microorganisms and showed moderate activity against the growth of methicillin-resistant Staphylococcus aureus (MRSA). 21,22-en-bafilomycin D and 21,22-en-9-hydroxybafilomycin D had potent activities in inhibiting the proliferation of glioma cells and the growth of MRSA. (C) 2017 Elsevier Ltd. All rights reserved.
• Gombamide A, a Cyclic Thiopeptide from the Sponge <i>Clathria gombawuiensis</i>
  作者：Jung-Kyun Woo、Ju-eun Jeon、Chang-Kwon Kim、Chung J. Sim、Dong-Chan Oh、Ki-Bong Oh、Jongheon Shin

  DOI：10.1021/np4003367

  日期：2013.7.26

  A new peptide, gombamide A (1), was isolated from the marine sponge Clathria gombawuiensis, collected from Korean waters. On the basis of the results of combined spectroscopic analyses, the structure of this compound was determined to be a cyclic C-terminally modified thiohexapeptide containing the unusual amino acid residues para-hydroxystyrylamide (pHSA) and pyroglutamic acid (pyroGlu). The absolute configurations of all amino acid residues were determined to be L by advanced Marfey's analysis. The new compound exhibited weak cytotoxicity against A549 and K562 cell lines as well as moderate inhibitory activity against Na+/K+-ATPase.