DAA-Glu | 95713-57-8

• 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: DAA-Glu
• 英文别名: D-glutamic acid；D-Glu
• CAS: 95713-57-8
• 化学式: C₁₄H₁₇N₅O₉
• 分子量: 399.317
• InChiKey: XISGXMPEFWFHIS-NKWVEPMBSA-N

物化性质

• 沸点：
  809.7±65.0 °C(Predicted)
• 密度：
  1.650±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  228.03
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  5'-[2-(R)-N-benzyloxy-N-(fluorenylmethyloxycarbonylaminoacetyl)amino-4-cyanobutanoylamino]-5'-deoxypseudouridine 在 indium(III) chloride 、 乙醛肟 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 63.0h， 生成 DAA-Glu
  参考文献：
  名称：

  Ugi型多组分反应全合成假尿嘧啶及其差向异构体

  摘要：

  完成了假尿嘧啶 ( 1 )的全合成，其特征在于不寻常的肟 Ugi 型多组分缩合以同时构建这种肽基核苷抗生素的二肽部分。在这个合成路线1中，通过假尿苷的9 个合成步骤的最长线性序列很容易获得。该策略可适用于多种假尿嘧啶类似物。

  DOI：

  10.1039/d2cc02442j

文献信息

• Cyclic lipodepsipeptides verlamelin A and B, isolated from entomopathogenic fungus Lecanicillium sp.
  作者：Kei-ichi Ishidoh、Hiroshi Kinoshita、Yasuhiro Igarashi、Fumio Ihara、Takuya Nihira

  DOI：10.1038/ja.2014.22

  日期：2014.6

  Verlamelin and its new derivative (verlamelin B) were isolated from fermentation broth of entomopathogenic fungus Lecanicillium sp. HF627. As the structural elucidation of verlamelin so far was only preliminary, we studied and determined the absolute structure of these two compounds to be cyclo(5S-hydroxytetradecanoic acid-D-alloThr/Ser-D-Ala-L-Pro-L-Gln-D-Tyr-L-Val). This is the first study that precisely analyzed the structure of verlamelin.

  来源于昆虫病原真菌Lecanicillium sp. HF627的发酵液中分离得到韦拉霉素及其新衍生物（韦拉霉素B）。由于目前对韦拉霉素的结构阐述仅是初步的，我们对其进行了研究并确定了这两种化合物的绝对构型为环状（5S-羟基十四酸-D-别苏氨酸/丝氨酸-D-丙氨酸-L-脯氨酸-L-谷氨酰胺-D-酪氨酸-L-缬氨酸）。这是首次对韦拉霉素结构进行精确分析的研究。
• New phenethylamine derivatives from Arenibacter nanhaiticus sp. nov. NH36AT and their antimicrobial activity
  作者：Yanping Chen、Jinshan Tang、Xixiang Tang、Chuanxi Wang、Yunyang Lian、Zongze Shao、Xinsheng Yao、Hao Gao

  DOI：10.1038/ja.2013.65

  日期：2013.11

  Five new phenethylamine (PEA) derivatives (1–5) were isolated from the strain of Arenibacter nanhaiticus sp. nov. NH36AT derived from the marine sediment of the South China Sea by bioassay-guided fractionation. Their structures were elucidated by spectroscopic methods including UV, IR, HR-MS and NMR. Interestingly, compounds 1–4 existed as enantiomers, which were resolved by chiral liquid chromatography. The resolved configuration of each enantiomer was assigned by the Marfey’s method. Of these compounds, 5 showed weak antimicrobial activity against Staphylococcus aureus and Bacillus subtilis with MIC values of 0.50 and 0.25 mg ml−1, respectively.

  通过生物测定导向分离，从南海海洋沉积物中分离出的新种NH36AT菌株中分离得到5个新的苯乙胺(PEA)衍生物(1-5)。通过光谱方法包括紫外、红外、高分辨质谱和核磁共振对其结构进行了鉴定。有趣的是，化合物1-4以对映异构体的形式存在，通过手性液相色谱进行了分离。每个对映异构体的构型通过Marfey法进行了确定。在这些化合物中，5号化合物对金黄色葡萄球菌和枯草芽孢杆菌显示出弱抗菌活性，最小抑菌浓度(MIC)值分别为0.50和0.25 mg/ml。
• Seven New and Two Known Lipopeptides as well as Five Known Polyketides: The Activated Production of Silent Metabolites in a Marine-Derived Fungus by Chemical Mutagenesis Strategy Using Diethyl Sulphate
  作者：Chang-Jing Wu、Chang-Wei Li、Cheng-Bin Cui

  DOI：10.3390/md12041815

  日期：——

  AD-2-1 is an antitumor fungal mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59. The G59 strain originally did not produce any metabolites with antitumor activities in MTT assays using K562 cells. Tracing newly produced metabolites under guidance of MTT assay and TLC analysis by direct comparison with control G59 extract, seven new (1–7) and two known (8–9) lipopeptides were isolated together with five known polyketides 10–14 from the extract of mutant AD-2-1. Structures of the seven new compounds including their absolute configurations were determined by spectroscopic and chemical evidences and named as penicimutalides A–G (1–7). Seven known compounds were identified as fellutamide B (8), fellutamide C (9), 1′-O-methylaverantin (10), averantin (11), averufin (12), nidurufin (13), and sterigmatocystin (14). In the MTT assay, 1–14 inhibited several human cancer cell lines to varying extents. All the bioassays and HPLC-photodiode array detector (PDAD)-UV and HPLC-electron spray ionization (ESI)-MS analyses demonstrated that the production of 1–14 in the mutant AD-2-1 was caused by the activated production of silent metabolites in the original G59 fungal strain. Present results provided additional examples for effectiveness of the chemical mutagenesis strategy using diethyl sulphate mutagenesis to discover new compounds by activating silent metabolites in fungal isolates.

  AD-2-1 是一种抗肿瘤真菌突变体，它是通过硫酸二乙酯诱变海洋源青霉菌 G59 获得的。在使用 K562 细胞进行的 MTT 试验中，G59 菌株原本不产生任何具有抗肿瘤活性的代谢物。在 MTT 试验和 TLC 分析的指导下，通过与对照 G59 提取物的直接比较，对新产生的代谢物进行了追踪，从突变体 AD-2-1 的提取物中分离出了七种新的（1-7）和两种已知的（8-9）脂肽，以及五种已知的多酮类化合物 10-14。通过光谱和化学证据确定了七种新化合物的结构及其绝对构型，并将其命名为青霉酰胺 A-G（1-7）。七个已知化合物被鉴定为fellutamide B (8)、fellutamide C (9)、1′-O-methylaverantin (10)、averantin (11)、averufin (12)、nidurufin (13) 和 sterigmatocystin (14)。在 MTT 试验中，1-14 对几种人类癌细胞株有不同程度的抑制作用。所有生物测定和高效液相色谱-光电二极管阵列检测器（PDAD）-紫外和高效液相色谱-电子喷雾电离（ESI）-质谱分析表明，突变体 AD-2-1 中 1-14 的产生是由原始 G59 真菌菌株中沉默代谢物的活化产生引起的。本研究结果为利用硫酸二乙酯诱变的化学诱变策略通过激活真菌分离物中的沉默代谢物来发现新化合物的有效性提供了更多实例。
• Chiral derivatization-enabled discrimination and on-tissue detection of proteinogenic amino acids by ion mobility mass spectrometry
  作者：Chengyi Xie、Yanyan Chen、Xiaoxiao Wang、Yuanyuan Song、Yuting Shen、Xin Diao、Lin Zhu、Jianing Wang、Zongwei Cai

  DOI：10.1039/d2sc03604e

  日期：——

  biological samples was proven in matrix-assisted laser desorption/ionization (MALDI) TIMS mass spectrometry imaging (MSI) as well by directly depositing 19 pairs of chiral AAs on a tissue slide following on-tissue derivatization. In addition, endogenous chiral amino acids were also detected and distinguished. The developed methods show compelling application prospects in biomarker discovery and biological

  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。
• Kyanamide, a new Ahp-containing depsipeptide from marine cyanobacterium Caldora penicillata
  作者：Kaori Ozaki、Arihiro Iwasaki、Kiyotake Suenaga、Toshiaki Teruya

  DOI：10.1016/j.tet.2019.04.046

  日期：2019.6

  Kyanamide (1), a new depsipeptide containing 3-amino-6-hydroxy-2-piperidone moiety, was isolated from the Caldora penicillata marine cyanobacterium collected in Okinawa. Its structure was determined by spectroscopic analysis and Marfey's analysis of acid hydrolysate. Kyanamide exhibited moderate cytotoxicity against HeLa S3 cells. 1 also exhibited potent protease inhibitory activity against elastase and chymotrypsin with IC50 values of 0.13 nM and 1.1 mu M. (C) 2019 Elsevier Ltd. All rights reserved.