L-FDAA-L-Lys | 194852-51-2

• 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-Lys
• CAS: 194852-51-2
• 化学式: C₁₅H₂₂N₆O₇
• 分子量: 398.376
• InChiKey: IPNKTVIENUIRHO-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  28.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  DL-赖氨酸 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (5-(((S)-1-amino-1-oxopropan-2-yl)amino)-2,4-dinitrophenyl)-D-lysine 、 L-FDAA-L-Lys
  参考文献：
  名称：

  离子淌度质谱法对蛋白氨基酸的手性衍生化鉴别和组织检测

  摘要：

  自从发现内源性D -AAs 作为几种代谢紊乱的潜在生物标志物以来，手性氨基酸 (AAs) 在生物体中的重要性已得到广泛认可。离子迁移谱-质谱法（IMS-MS）的手性分析具有速度快、灵敏度高等优点，但仍处于起步阶段。此处，N α -(2,4-二硝基-5-氟苯基)- L-丙氨酰胺 (FDAA) 衍生化与俘获离子淌度质谱 (TIMS-MS) 相结合，用于手性 AA 分析。我们首次展示了在单个固定条件 TIMS-MS 运行中同时分离 19 对手性蛋白氨基酸。通过直接注入 TIMS-MS 提出了这种方法对小鼠大脑提取物的实用性。基质辅助激光解吸/电离 (MALDI) TIMS 质谱成像 (MSI) 以及在组织衍生化后将 19 对手性 AA 直接沉积在组织载玻片上证明了复杂生物样品的强大分离能力。此外，还检测并区分了内源性手性氨基酸。所开发的方法在生物标志物发现和生物学研究中显示出引人注目的应用前景。

  DOI：

  10.1039/d2sc03604e

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。
• Stereochemical Elucidation of New Sagittamides C - F from a Didemnid Ascidian
  作者：Sarah C. Lievens、Brandon I. Morinaka、Tadeusz F. Molinski

  DOI：10.1071/ch10059

  日期：——

  Four new minor congeners, sagittamides C–F, were isolated from an unidentified Didemnid tunicate that previously afforded sagittamides A and B. The structures were determined by interpretation of spectroscopic data, degradation to amino acids, and comparisons with sagittamide A. An unexpected change in relative configuration of the hexacetoxy C5–C10 stereoelement is present in sagittamides D and F. A tentative assignment of configuration was possible through a systematic deduction based on analysis of 13C NMR data and symmetry considerations.

  通过对光谱数据的解释、氨基酸的降解以及与箭头酰胺 A 的比较，确定了箭头酰胺 C-F 的结构。根据对 13C NMR 数据的分析和对称性的考虑，通过系统推导，可以初步确定其构型。
• 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.
• Sungsanpin, a Lasso Peptide from a Deep-Sea Streptomycete
  作者：Soohyun Um、Young-Joo Kim、Hyuknam Kwon、He Wen、Seong-Hwan Kim、Hak Cheol Kwon、Sunghyouk Park、Jongheon Shin、Dong-Chan Oh

  DOI：10.1021/np300902g

  日期：2013.5.24

  Sungsanpin (1), a new 15-amino-acid peptide, was discovered from a Streptomyces species isolated from deep-sea sediment collected off Jeju Island, Korea. The planar structure of 1 was determined by 1D and 2D NMR spectroscopy, mass spectrometry, and UV spectroscopy. The absolute configurations of the stereocenters in this compound were assigned by derivatizations of the hydrolysate of 1 with Marfey's reagents and 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate, followed by LC-MS analysis. Careful analysis of the ROESY NMR spectrum and three-dimensional structure calculations revealed that sungsanpin possesses the features of a lasso peptide: eight amino acids (-Gly(1)-Phe-Gly-Ser-Lys-Pro-Ile-Asp(8)-) that form a cyclic peptide and seven amino acids (-Ser(9)-Phe-Gly-Leu-Ser-Trp-Leu(15)) that form a tail that loops through the ring. Sungsanpin is thus the first example of a lasso peptide isolated from a marine-derived microorganism. Sungsanpin displayed inhibitory activity in a cell invasion assay with the human lung cancer cell line A549.