N^α-formyl-L-lysine | 19729-28-3

• 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: N^α-formyl-L-lysine
• 英文别名: N^α-formyllysine；N(α)-Formyl-L-lysin；Formyl-l-lysine；(2S)-6-amino-2-formamidohexanoic acid
• CAS: 19729-28-3
• 化学式: C₇H₁₄N₂O₃
• 分子量: 174.2
• InChiKey: LIEIRDDOGFQXEH-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N^α-formyl-L-lysine 在 吡啶 、 盐酸 作用下， 生成 生物胞素
  参考文献：
  名称：

  Synthesis of Biocytin

  摘要：

  DOI：

  10.1021/ja01128a039
• 作为产物：
  描述：

  N^α-formyl-N^Ε-CBZ-L-lysine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以55%的产率得到N^α-formyl-L-lysine
  参考文献：
  名称：

  三氯环氧乙烷的水分解机理

  摘要：

  三氯乙烯 (TCE) 氧化物的水溶液分解显示涉及 pH 无关和水合氢离子依赖区域。C-C 键断裂是所有 pH 值下的主要反应。在所研究的条件下，TCE 氧化物的消失是 CO 形成的速率决定步骤。CO和三种羧酸（HCO2H、Cl2CHCO2H和乙醛酸）的产物分布在-1.5-14的pH范围内没有显着变化，通常，即使水解机制从水合氢离子依赖变为pH无关. 基于 H218O 和 H 掺入的结果以及 TCE 氧化物与赖氨酸在 H216O 和 H218O 中反应的产物的鉴定，阐明了 TCE 氧化物的水合氢离子依赖性和 pH 无关水解的机制。在不依赖 pH 的水解中，

  DOI：

  10.1021/ja9914240

文献信息

• Research on Alkoxythiobenzamides, III: Synthesis of New 3,4,5-Trimethoxythiobenzamides and Related Thiomorpholides with Potential Antisecretory and Antiulcer Activity
  作者：Carlo Farina、Renato Pellegata、Mario Pinza、Giorgio Pifferi

  DOI：10.1002/ardp.19813140204

  日期：——

  trithiozine, were prepared by reaction of primary amines, acyclic secondary amines and various amino acids with methyl 3,4,5‐trimethoxydithiobenzoate (1a) or (3,4,5‐trimethoxythiobenzoylthio)acetic acid (1b). Some thiomorpholides 7 of alkoxyphenylalkanoic acids were prepared by thionation of the corresponding amides or from the appropriate ketones by the Willgerodt‐Kindler reaction.

  作为合成新型抗分泌和抗溃疡烷氧基硫代苯甲酰胺项目的一部分，3,4,5-三甲氧基硫代苯甲酰胺 2 和 3 是三硫嗪的类似物，通过伯胺、无环仲胺和各种氨基酸与甲基 3 反应制备， 4,5-三甲氧基二硫代苯甲酸酯 (1a) 或 (3,4,5-三甲氧基硫代苯甲酰硫基) 乙酸 (1b)。一些烷氧基苯基链烷酸的硫代吗啉 7 是通过相应的酰胺或适当的酮通过 Willgerodt-Kindler 反应进行硫化而制备的。
• Identification of the Carboxymethyllysine Residue in the Advanced Stage of Glycated Human Serum Albumin.
  作者：Masaya TAKANASHI、Tamiko SAKURAI、Seishi TSUCHIYA

  DOI：10.1248/cpb.40.705

  日期：——

  As an advanced stage of glycation, glycated human serum albumin (G-HSA; glucose content, 2mol of 5-hydroxymethylfufural equivalent/mol of HSA) was incubated at 37°C up to 30d in 0.2M phosphate buffer, pH 7.4, with 100 μM Fe3+. G-HSA incubated for 30d (G-HSA-30(Fe)) was subsequently hydrolyzed at 110°C for 24h in 6N HCl. In the hydrolysate, N2-carboxymethyllysine (CML) was identified by cochromatography with synthesized CML on an amino acid analyzer. pI of HSA (4.8) shifted to 4.5 in G-HSA. A more acidic fraction, pI 4.3, appeared in G-HSA-30(Fe). CML content (mol of CML/mol of HSA) of HSA and G-HSA was as follows; 0 in HSA, 0.2 in HSA-30(Fe), 0.4 in G-HSA and 1.5 in G-HSA-30(Fe) pI 4.3. The amino acid compositions also changed in lysine, arginine and tyrosine at the advanced stage of the reaction.

  作为糖化的高级阶段，糖化人血清白蛋白（G-HSA；葡萄糖含量为2mol的5-羟甲基糠醛当量/mol的HSA）在37°C的0.2M磷酸盐缓冲液（pH 7.4）中与100 μM Fe3+一起孵育长达30天。孵育30天后的G-HSA（G-HSA-30(Fe)）随后在6N HCl中于110°C水解24小时。在水解产物中，通过与合成的CML在氨基酸分析仪上共同色谱，识别出了N2-羧甲基赖氨酸（CML）。HSA的等电点（pI）从4.8变为G-HSA的4.5。在G-HSA-30(Fe)中出现了一个更酸性的部分，pI为4.3。HSA和G-HSA中的CML含量（CML的摩尔数与HSA的摩尔数之比）如下：HSA中为0，HSA-30(Fe)中为0.2，G-HSA中为0.4，在G-HSA-30(Fe)的pI 4.3中为1.5。随着反应的进行，氨基酸组成在赖氨酸、精氨酸和酪氨酸方面也发生了变化。
• Compounds and methods for therapeutic intervention in preventing diabetic complications and procedures for assessing a diabetic's risk of developing complications and determining the efficacy of therapeutic intervention
  申请人：——

  公开号：US20020111291A1

  公开（公告）日：2002-08-15

  Disclosed is a class of compounds which inhibit the enzymatic conversion of fructose-lysine into fructose-lysine-3-phosphate in an ATP dependent reaction in a newly discovered metabolic pathway. According to the normal functioning on this pathway, fructose-lysine-3-phosphate (FL3P) is broken down to form free lysine, inorganic phosphate and 3-deoxyglucosone (3DG), the latter being a reactive protein modifying agent. 3DG can be detoxified by reduction to 3-deoxyfructose (3DF), or it can react with endogenous proteins to form advanced glycation end-product modified proteins (AGE-proteins), which are believed to be a contributing cause of diabetic complications. Also disclosed are therapeutic methods of using such inhibitors to reduce formation of AGE-proteins and thereby lessen, reduce and delay diabetic complications and the effects of glycogen storage diseases, including Fanconi's syndrome. Methods for assessing a diabetic's risk of developing complications and for determining the efficacy of the disclosed inhibitor therapy by measuring the ratio of 3DG to 3DF in a biological sample following an oral dose of a fructose-lysine-containing food product are also disclosed.

  本文披露了一类化合物，可以抑制酶催化将果糖赖氨酸转化为果糖赖氨酸-3-磷酸酯的反应，这是一种新发现的代谢途径中依赖ATP的反应。根据该途径的正常功能，果糖赖氨酸-3-磷酸酯（FL3P）被分解为游离赖氨酸、无机磷酸盐和3-脱氧葡萄糖酮（3DG），后者是一种具有反应性的蛋白质修饰剂。3DG可以通过还原为3-脱氧果糖（3DF）来解毒，也可以与内源蛋白质反应形成高级糖基化终产物修饰的蛋白质（AGE-蛋白），据信这是糖尿病并发症的一个促发因素。此外，还披露了使用这种抑制剂的治疗方法，以减少AGE-蛋白的形成，从而减轻、减少和延迟糖尿病并发症和糖原贮积病（包括范科尼综合征）的影响。还披露了通过在口服含果糖赖氨酸的食品后测量生物样品中3DG与3DF比值来评估糖尿病患者发生并发症的风险和确定披露的抑制剂疗法的疗效的方法。
• Optimization of the Synthesis of the Cross-Linked Amino Acid Ornithinoalanine and Nuclear Magnetic Resonance Characterization of Lysinoalanine and Ornithinoalanine
  作者：Giovanna Boschin、Leonardo Scaglioni、Anna Arnoldi

  DOI：10.1021/jf980869p

  日期：1999.3.1

  unnatural amino acids that can be formed in food submitted to thermal treatment, especially in alkaline conditions. The paper presents an optimization of the synthetic procedure for the preparation of a standard of OAL that could be very useful to study the toxicological and nutritional consequences of the presence of OAL in food. In the meantime, it was possible to develop a method based on nuclear magnetic

  赖氨酸丙氨酸（LAL）和鸟氨酸丙氨酸（OAL）是非天然氨基酸，可以在经过热处理的食物中形成，尤其是在碱性条件下。本文介绍了用于制备OAL标准品的合成方法的优化方法，该方法对于研究食品中存在OAL的毒理学和营养后果非常有用。同时，有可能开发一种基于核磁共振的方法，用于不衍生化的LAL和OAL的非对映异构体表征。对这种方法的兴趣是基于LAL的两种非对映异构体在肾毒性方面的已知差异。
• Le blocage de la lysine par la réaction de M<scp>AILLARD</scp>. I. Synthèse de N-(désoxy-1-<scp>D</scp>-fructosyl-1)- et N-(désoxy-1-<scp>D</scp>-lactulosyl-1)-<scp>L</scp>-lysines
  作者：P. A. Finot、J. Mauron

  DOI：10.1002/hlca.19690520609

  日期：——

  The authors describe a specific method for the preparation of Nϵ-(1-deoxy-D-fructosyl)-L-lysine, Nα-(1-deoxy-D-fructosyl)-L-lysine, their formyl derivatives, and Nα-formyl-ϵ-(1-deoxy-D-lactulosyl)-L-lysine, as well as Nα, Nϵ-di-(1-deoxy-D-fructosyl)-L-lysine. After purification by cation-exchange chromatography using volatile pyridine-acetic acid or pyridine-formic acid buffers, these compounds are

  作者描述了一种具体的制备N for-（1-脱氧-D-果糖基）-L-赖氨酸，Nα-（1-脱氧-D-果糖基）-L-赖氨酸，它们的甲酰基衍生物和Nα-甲酰基的方法。 -ϵ-（1-脱氧-D-乳糖基）-L-赖氨酸，以及Nα，Nϵ-二-（1-脱氧-D-果糖基）-L-赖氨酸。在使用挥发性吡啶-乙酸或吡啶-甲酸缓冲液通过阳离子交换色谱法纯化后，以纯净状态获得这些化合物。通过薄层色谱和纸电泳可以快速分离和鉴定这些赖氨酸衍生物。