DL-犬尿氨酸硫酸盐 | 2126-91-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: DL-犬尿氨酸硫酸盐
• 中文别名: DL-硫酸犬尿素
• 英文名称: DL-kynurenine sulfate salt
• 英文别名: D,L-kynurenine sulfate；KN sulfate salt；DL-kynurenin; sulfate；DL-Kynurenin; Sulfat；DL-Kynurenine sulfate；2-amino-4-(2-aminophenyl)-4-oxobutanoic acid;sulfuric acid
• CAS: 2126-91-2；66866-42-0
• 化学式: C₁₀H₁₂N₂O₃*H₂O₄S
• 分子量: 306.296
• InChiKey: KAXRWMOLNJZCEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  189
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• WGK Germany：
  3
• 海关编码：
  2922499990
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319

反应信息

• 作为反应物：
  描述：

  DL-犬尿氨酸硫酸盐 在 碳酸氢钠 作用下， 反应 24.0h， 以26%的产率得到4-oxo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid
  参考文献：
  名称：

  Novel human lens metabolites from normal and cataractous human lenses

  摘要：

  4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human lens samples. Their structures are consistent with those derived from the major human lens UV filters kynurenine and 3-hydroxykynurenine, and it is proposed that these compounds also play a role as UV filters. These metabolites were isolated in pmol/mg levels (dry mass) in lenses. 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine were found to be unstable at physiological pH. Other potential metabolites, glutathionyl-3-hydroxykynurenine, kynurenine yellow and 3-hydroxykynurenine yellow, were not detected in either normal or cataractous lenses. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.133

文献信息

• Kinetics and mechanism of thermal decomposition of kynurenines and biomolecular conjugates: Ramifications for the modification of mammalian eye lens proteins
  作者：Lyudmila V. Kopylova、Olga A. Snytnikova、Elena I. Chernyak、Sergey V. Morozov、Malcolm D. E. Forbes、Yuri P. Tsentalovich

  DOI：10.1039/b903196k

  日期：——

  Thermal degradation reactions of kynurenine (KN), 3-hydroxykynurenine (3OHKN), and several adducts of KN, to amino acids and reduced glutathione (GSH) have been studied at physiological temperature. These compounds are all implicated in age-related mammalian eye lens cataract formation at the molecular level. The main reaction pathway for both KN and 3OHKN is deaminationviaβ-elimination to carboxyketoalkenes

  的热降解反应 犬尿氨酸（KN），3-羟基犬尿氨酸（3OHKN）以及KN与氨基酸和还原型谷胱甘肽（GSH）的几种加合物已在生理温度下进行了研究。这些化合物在分子水平上均与年龄相关的哺乳动物晶状体白内障形成有关。KN和3OHKN的主要反应途径是通过β-消除作用脱羧成羧基酮烯烃CKA和3OHCKA。这些反应在低于〜8的pH值下显示出较弱的pH依赖性，而在高于该值时则显示出很强的pH依赖性。3OHKN结构的脱氨速度比KN快。提出了一种脱氨反应的机理，涉及一种芳基羰基烯醇/烯醇酸根离子，这在结构，动力学和pH数据上都得到了强有力的支持。赖氨酸，他的，半胱氨酸还研究了CKA部分的GSH加合物。发现Lys加合物在37°C的200小时内相对稳定，而其他加合物则观察到明显的降解。将根据晶状体蛋白质的已知翻译后修饰反应来讨论结果，并将其与在蛋白质存在下涉及KN和相关化合物的孵育研究进行比较。
• Photophysics and Photochemistry of the UV Filter Kynurenine Covalently Attached to Amino Acids and to a Model Protein
  作者：Peter S. Sherin、Jakob Grilj、Lyudmila V. Kopylova、Vadim V. Yanshole、Yuri P. Tsentalovich、Eric Vauthey

  DOI：10.1021/jp104485k

  日期：2010.9.16

  The photophysics and photochemistry of kynurenine (KN) covalently bound to the amino acids lysine, cysteine, and histidine, the antioxidant glutathione, and the protein lysozyme have been studied by optical spectroscopy with femto- and nanosecond time resolution. The fluorescence quantum yield of the adducts of KN to amino acids is approximately 2 times higher than that of the free KN in solution;

  犬尿氨酸（KN）与赖氨酸，半胱氨酸和组氨酸，氨基酸，抗氧化剂谷胱甘肽和蛋白质溶菌酶共价结合的光物理化学和光化学已经通过飞秒和纳秒级的光谱学进行了研究。KN与氨基酸的加合物的荧光量子产率比溶液中游离KN的荧光量子产率高约2倍。附着在蛋白质上的KN的荧光量子产率提高了7倍。S 1KN修饰的溶菌酶的动态状态揭示了一个多相衰减，其时间常数从1 ps到2 ns广泛分布。还观察到与溶菌酶结合的KN的三重态产量增加；三重态迅速发生分子内衰变。获得的结果表明，KN与氨基酸和蛋白质共价连接后，其光化学活性增加，这可能有助于人类晶状体中氧化应激的发展，而氧化应激是白内障发病的主要诱因。
• Cosmetic composition comprising kynurenine
  申请人：Uchikuga, Saburoh

  公开号：EP1038516A1

  公开（公告）日：2000-09-27

  The invention relates to an outdoor cosmetic comprising kynurenine (derivative) as an effective ingredient and serving for retaining skin health under exposure to ultraviolet ray, not by inhibiting tyrosinase activity but by actively utilizing tyrosinase activity and allowing the intermediate products in the course of black melanin generation to react with kynurenine (derivative) to generate safe pigments in yellowish brown to red under inhibition of the generation of black melanin.

  本发明涉及一种户外化妆品，其中含有作为有效成分的犬尿氨酸（衍生物），并可在紫外线照射下保持皮肤健康，其方法不是抑制酪氨酸酶的活性，而是积极利用酪氨酸酶的活性，让黑色素生成过程中的中间产物与犬尿氨酸（衍生物）反应，在抑制黑色素生成的情况下生成黄棕色至红色的安全色素。
• IN VITRO METHOD FOR THE DETERMINATION OF NEURODEGENERATIVE DISEASES
  申请人：SALION GmbH

  公开号：EP3635409A1

  公开（公告）日：2020-04-15
• US6265442B1
  申请人：——

  公开号：US6265442B1

  公开（公告）日：2001-07-24