6-硝基-2-氨苯酚-4-磺酸 | 496-93-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 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
• 中文名称: 6-硝基-2-氨苯酚-4-磺酸
• 中文别名: O-氨基-L-高丝氨酸；副刀豆氨酸
• 英文名称: l-canaline
• 英文别名: L-2-amino-4-(aminooxy)butanoic acid；L-Can；O-amino-L-homoserine；O-Amino-L-homoserin；O-Amino-L-homoserin; (S)-O-(3-Amino-3-carboxy-propyl)-hydroxylamin；(S)-O-(3-Amino-3-carboxy-propyl)-hydroxylamin；L-2-amino-4-(aminooxy)butyrate；(2S)-4-aminooxy-2-azaniumylbutanoate
• CAS: 496-93-5
• 化学式: C₄H₁₀N₂O₃
• mdl: MFCD00057642
• 分子量: 134.135
• InChiKey: FQPGMQABJNQLLF-VKHMYHEASA-N

物化性质

• 密度：
  1.298
• 溶解度：
  DMSO 中≤1mg/ml
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  98.6
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 安全说明：
  S22,S24/25
• 海关编码：
  2922509090
• 储存条件：
  -20°C，干燥，密封

制备方法与用途

生物活性

L-Canaline 是一种非蛋白质氨基酸，存在于许多豆科植物中。它是由 L-canavanine 及其精氨酸酶催化的毒性代谢产物，并且是有效且不可逆的鸟氨酸氨基转移酶抑制剂。L-Canaline 能够抑制疟原虫恶性疟原虫的生长，IC50 值为 297 nM。此外，它还具有抗癌和抗增殖作用。

靶点

• IC50: 297 nM (恶性疟原虫); 鸟氨酸氨基转移酶

体外研究

L-Canaline 处理能够抑制 PBMCs 在由 phorbol 12-myristate-13-acetate (PMA) 或混合淋巴细胞反应刺激后的增殖。在 PMA 刺激的细胞中，IC50 值为 0.26 mM，这效果最为显著；相比之下，在通过混合淋巴细胞反应刺激的细胞中，IC50 值为 0.54 mM。L-Canaline 在 astrocytes 和星形细胞瘤细胞中以竞争性方式抑制 L-赖氨酸的通量（Ki值为 4.6 mM）。

体内研究

在雄性 Wistar 大鼠的延髓组织中，L-Canaline 可减少天冬氨酸含量，但不会影响该非蛋白质氨基酸的诱发释放。向雄性 Sprague-Dawley 大鼠的隔区注射 100 μg L-Canaline，在动物杀掉后 1 小时内，观察到隔区组织中的鸟氨酸氨基转移酶活性减少了约 90%。

反应信息

• 作为反应物：
  描述：

  6-硝基-2-氨苯酚-4-磺酸 、 乙醛酸 生成 2-amino-4-[(E)-carboxymethylideneamino]oxybutanoic acid
  参考文献：
  名称：

  ROSENTHAL, GERALD A.;BERGE, MILAN A.;BLEILER, JOHN A., BIOCHEM. SYST. AND ECOL., 17,(1989) N, C. 203-206

  摘要：

  DOI：
• 作为产物：
  描述：

  L-刀豆氨酸 在 arginase [EC 3.5.3.1] 、 水 作用下， 生成 6-硝基-2-氨苯酚-4-磺酸
  参考文献：
  名称：

  Structure−Activity Studies of l-Canaline-Mediated Inhibition of Porcine Alanine Aminotransferase

  摘要：

  L-Canaline [L-2-amino-4-(aminooxy)butanoic acid] (L-CAN) and a family of eleven structurally related analogs were synthesized and evaluated for their inhibitory effect on PLP-dependent alanine aminotransferase (AlaAT) (EC 2.6.1.2) obtained from porcine heart. These congeners were selected to determine the stereochemical, aliphatic chain length, and aminooxy substitutional effects on L-CAN-mediated inhibition of AlaAT activity. L-CAN was the most effective inhibitor of the tested compounds; 10(-7) M L-CAN elicited a 55% reduction in AlaAT activity after a 5 min exposure. This deleterious effect results from the ability of L-CAN to react avidly with the PLP moiety of the enzyme to form a stable, L-CAN-PLP oxime. In contrast, the methyl and ethyl esters of L-CAN reduced AlaAT activity by only 8% and 6%, respectively. While all of the L-enantiomeric forms of the tested compound were more potent AlaAT inhibitors than their corresponding D-stereoisomers, the D-enantiomers, particularly D-canaline, were active. Chain shortening or lengthening dramatically curtailed L-CAN-mediated loss in AlaAT activity, but the replacement of the cr-amino group with a hydrogen was of little consequence in this regard. AlaAT was treated with L-CAN in the presence of free PLP to assess PLP capacity to protect AlaAT against 10(-7) M L-CAN-dependent inactivation. L-CAN retained approximately two-thirds of its inhibitory ability in the presence of equimolar PLP, but AlaAT inhibition was reduced 90% by a 10-fold excess of PLP over L-CAN.

  DOI：

  10.1021/tx9600199

文献信息

• Electronic Case-Report Forms of Symptoms and Impairments of Peripheral Neuropathy
  作者：Peter J. Dyck、David W. Turner、Jenny L. Davies、Peter C. O’Brien、P. James B. Dyck、Cynthia A. Rask

  DOI：10.1017/s0317167100002043

  日期：2002.8

  For the conduct of controlled clinical trials, epidemiologic surveys or even of medical practice of varieties of peripheral neuropathy, the usefulness, error rate and cost-effectiveness of scannable case-report forms has not been studied. Materials and

  The overall performance, the frequency of the problems identified and corrected, and the time saved from use of a standard paper case report form was evaluated in multicenter treatment trials, single center epidemiologic surveys and in our neurologic practice. The paper case report form (Clinical Neuropathy Assessment [CNA]) for pen entry at study medical centers for patient, disease and demographic information (Lower Limb Function [LLF] and Neuropathy Impairment Score [NIS]) can be faxed to a core Reading and Quality Assurance Center where the form and data is electronically and interactively evaluated and corrected, if needed, by participating medical centers before electronic entry into database.

  1) The approach provides a standard, scannable paper case report form for pen entry of neuropathy symptoms, impairments and disability at the bedside or in the office which is retained as a source document at the participating medical center but a facsimile can be transferred instantaneously, its data can be programmed, interactively evaluated, modified and stored while maintaining an audit trail; 2) it allowed efficient and accurate reading, transfer, analysis, and storage of data of more than 15,000 forms used in multicenter trials; 3) in 500 consecutive CNA evaluations, software programs identified and facilitated interactive corrections of omissions, discrepancies, and disease and study inconsistencies, introducing only a few readily identified and corrected entry errors; and 4) use of programmed, as compared to non-programmed assessment, was more accurate than double keyboard entry of data and was approximately five times faster.

  背景和目的：对于外周神经病的临床对照试验、流行病学调查甚至医疗实践，尚未研究过可扫描病例报告表的实用性、错误率和成本效益。材料与方法：我们在多中心治疗试验、单中心流行病学调查和神经科临床实践中评估了标准纸质病例报告表的总体性能、发现和纠正问题的频率以及使用该表所节省的时间。纸质病例报告表（临床神经病变评估[CNA]）用于研究医疗中心的患者、疾病和人口统计学信息（下肢功能[LLF]和神经病变损伤评分[NIS]）的钢笔输入，可传真至核心阅读和质量保证中心，在该中心，参与研究的医疗中心将对表格和数据进行电子和交互式评估，并在需要时进行更正，然后再以电子方式输入数据库。观察和结论1）该方法提供了一种标准的、可扫描的纸质病例报告表，用于在床边或办公室用笔输入神经病变症状、损伤和残疾情况，该报告表作为原始文件保留在参与的医疗中心，但传真可以即时传输，其数据可以编程、交互式评估、修改和存储，同时保持审计跟踪；2）该方法允许高效、准确地读取、传输、分析和存储多中心试验中使用的 15,000 多份表格的数据；3）在连续 500 次的 CNA 评估中，软件程序识别并促进了对遗漏、差异、疾病和研究不一致的交互式纠正，只引入了少数易于识别和纠正的输入错误；以及 4）与非程序评估相比，使用程序评估比双键输入数据更准确，速度快约五倍。
• Inhibitors of nitric oxide biosynthesis
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05318992A1

  公开（公告）日：1994-06-07

  The present invention is a method of treating hypotension and shock using select ornithine or N.sup.G -arginine derivatives.

  本发明是一种使用特定的鸟氨酸或N.sup.G-精氨酸衍生物治疗低血压和休克的方法。
• Characterization of AmtA, an amidinotransferase involved in the biosynthesis of phaseolotoxins
  作者：Mi Li、Li Chen、Zixin Deng、Changming Zhao

  DOI：10.1002/2211-5463.12071

  日期：2016.6

  Phaseolotoxins (PHTs), which are produced by Pseudomonas, belong to a family of phosphoramidate natural products. Two nonproteinogenic amino acid precursors, Nδ(N′‐sulfo‐diaminophosphinyl)‐ornithine (PSOrn) and homoarginine (hArg), are involved in biosynthesis of PHTs. Amidinotransferase AmtA catalyses the formation of hArg, with arginine and lysine as substrates. AmtA was overexpressed and purified in an Escherichia

  由假单胞菌（PSeudomonas）产生的菜豆毒素（PHT）属于氨基磷酸酯天然产物的家族。两个nonproteinogenic的氨基酸前体，N δ（N'-硫代diaminophosphinyl）鸟氨酸（PSOrn）和高精氨酸（ħ精氨酸），参与PHTs的生物合成。氨基转移酶AmtA以精氨酸和赖氨酸为底物催化h Arg的形成。AmtA在大肠杆菌系统中过表达和纯化。一种在体外酶测定法显示，它比某些其他酰胺基转移酶具有更严格的底物特异性。定点诱变实验表明，AmtA Met243His244突变是替代方案，而Met246对转酰胺基化活性至关重要。
• Synthesis of L-canaline and .gamma.-functional 2-aminobutyric acid derivatives
  作者：Alvydas J. Ozinskas、Gerald A. Rosenthal

  DOI：10.1021/jo00376a001

  日期：1986.12
• Kitagawa, Journal of Biochemistry, 1936, vol. 24, p. 107,109
  作者：Kitagawa

  DOI：——

  日期：——