H-Lys-OH

• 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: H-Lys-OH
• 英文别名: S-(+)-lysine, monoprotonated；lysine；H-K-OH；LysH(+)；[(2S)-2,6-diaminohexanoyl]oxidanium
• 化学式: C₆H₁₅N₂O₂
• 分子量: 147.197
• InChiKey: KDXKERNSBIXSRK-YFKPBYRVSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  91
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  H-Lys-OH 在 二正丙胺 作用下， 以 gas 为溶剂， 生成 L-赖氨酸
  参考文献：
  名称：

  Kinetic and thermodynamic considerations of the bracketing method: Entropy-driven proton-transfer reactions in a Fourier transform mass spectrometer

  摘要：

  AbstractSeveral reports of experimentally derived proton affinity values and gas‐phase basicity values for amino acids and peptides have recently appeared in the literature. Here, we show that the thermodynamic quantity that is measured by the Fourier transform mass spectrometry proton transfer bracketing of amino acids and peptides is gas‐phase basicity and not proton affinity. Both experimental and theoretical evidence supports this conclusion. The difference between the values determined by proton transfer bracketing measurements for lysine versus leucine is consistent with a difference in gas‐phase basicity rather than proton affinity. The rate of proton transfer from protonated lysine to a series of reference compounds have been measured. Entropy‐driven, endothermic proton transfer is found to occur at the collision rate. Recent ab initio and semi‐empirical calculations of the proton affinity of lysine are found to agree with the value that is derived from bracketing studies when one assumes that gas‐phase basicity is measured. While entropy‐driven reactions have been observed previously in high‐pressure mass spectrometers, this is the first evidence for such reactions at low pressure in a Fourier transform mass spectrometer.

  DOI：

  10.1002/oms.1210281236
• 作为产物：
  描述：

  N^α-benzoyl-L-lysine 在 盐酸 作用下， 生成 H-Lys-OH 、 苯甲酸
  参考文献：
  名称：

  Muzalewski, Feliks; Ciurak, Marek, Polish Journal of Chemistry, 1983, vol. 57, # 7-9, p. 931 - 940

  摘要：

  DOI：

文献信息

• Biosynthesis of Pipecolic Acid by RapL, a Lysine Cyclodeaminase Encoded in the Rapamycin Gene Cluster
  作者：Gregory J. Gatto,、Michael T. Boyne、Neil L. Kelleher、Christopher T. Walsh

  DOI：10.1021/ja0587603

  日期：2006.3.1

  some release and rebinding of NAD+ during catalytic cycles. Through the use of isotopically labeled substrates, we have confirmed mechanistic details of the cyclodeaminase reaction, including loss of the alpha-amine and retention of the hydrogen atom at the alpha-carbon. In addition to the characterization of a critical enzyme in the biosynthesis of a medically important class of natural products,

  雷帕霉素、FK506 和 FK520 是免疫抑制剂大环内酯天然产物，主要由基于聚酮化合物的核心结构组成。通过非核糖体肽合成酶将单个非蛋白原性哌可酸残基安装到支架中，该酶还在该氨基酸的羰基上执行随后的大环化步骤。已经假设哌可酸是由赖氨酸通过环脱氨酶 RapL/FkbL 产生的。在此，我们报告了 RapL 的异源过表达和纯化，并验证了其通过涉及氧化还原催化的环脱氨反应将 L-赖氨酸转化为 L-哌啶酸的能力。RapL 也接受 L-鸟氨酸作为底物，尽管催化效率显着降低。假定周转率包括在 α-胺处的可逆氧化、内部环化、并随后重新还原环状 delta1-哌啶-2-羧酸中间体。分离后，RapL 具有约 0.17 当量的紧密结合的 NAD+，表明该酶在大肠杆菌中过量生产时未完全加载。在存在外源 NAD+ 的情况下，初始速率提高 8 倍，辅因子的 Km 为 2.3 microM，与催化循环期间 NAD+ 的
• Molecular recognition of methylated amino acids and peptides by Pillar[6]MaxQ
  作者：David King、Chelsea R. Wilson、Lukas Herron、Chun-Lin Deng、Shams Mehdi、Pratyush Tiwary、Fraser Hof、Lyle Isaacs

  DOI：10.1039/d2ob01487d

  日期：——

  recognition properties of Pillar[n]MaxQ (P[n]MQ) toward a series of (methylated) amino acids, amino acid amides, and post-translationally modified peptides by a combination of 1H NMR, isothermal titration calorimetry, indicator displacement assays, and molecular dynamics simulations. We find that P6MQ is a potent receptor for N-methylated amino acid side chains. P6MQ recognized the H3K4Me3 peptide with

  我们通过结合1 H NMR、等温滴定量热法，报告了 Pillar[ n ]MaxQ (P[ n ]MQ) 对一系列（甲基化）氨基酸、氨基酸酰胺和翻译后修饰肽的分子识别特性、指示剂位移测定和分子动力学模拟。我们发现 P6MQ 是N-甲基化氨基酸侧链的有效受体。 P6MQ 在磷酸盐缓冲盐水中识别K d = 16 nM 的 H3K4Me 3肽。
• Aminoacyl-tRNA Synthesis
  作者：Michael Ibba、Dieter Söll

  DOI：10.1146/annurev.biochem.69.1.617

  日期：2000.6

  ▪ Abstract  Aminoacyl-tRNAs are substrates for translation and are pivotal in determining how the genetic code is interpreted as amino acids. The function of aminoacyl-tRNA synthesis is to precisely match amino acids with tRNAs containing the corresponding anticodon. This is primarily achieved by the direct attachment of an amino acid to the corresponding tRNA by an aminoacyl-tRNA synthetase, although intrinsic proofreading and extrinsic editing are also essential in several cases. Recent studies of aminoacyl-tRNA synthesis, mainly prompted by the advent of whole genome sequencing and the availability of a vast body of structural data, have led to an expanded and more detailed picture of how aminoacyl-tRNAs are synthesized. This article reviews current knowledge of the biochemical, structural, and evolutionary facets of aminoacyl-tRNA synthesis.

  摘要：氨酰-tRNA是翻译的底物，对于决定遗传密码如何解释为氨基酸至关重要。氨酰-tRNA合成的功能是将氨基酸与含有相应反密码子的tRNA精确匹配。这主要通过氨酰-tRNA合成酶直接将氨基酸附加到相应的tRNA上实现，尽管内在的校对和外在的编辑在几种情况下也是必不可少的。最近对氨酰-tRNA合成的研究主要是由于整个基因组测序的出现和大量结构数据的可用性，已经扩展和详细描述了氨酰-tRNA合成的过程。本文回顾了氨酰-tRNA合成的生化、结构和进化方面的当前知识。
• Pathway of lysine degradation in Fusobacterium nucleatum
  作者：H A Barker、J M Kahn、L Hedrick

  DOI：10.1128/jb.152.1.201-207.1982

  日期：1982.10

  Lysine was fermented by Fusobacterium nucleatum ATCC 25586 with the formation of about 1 mol each of acetate and butyrate. By the use of [1-14C]lysine or [6-14C]lysine, acetate and butyrate were shown to be derived from both ends of lysine, with acetate being formed preferentially from carbon atoms 1 and 2 and butyrate being formed preferentially from carbon atoms 3 to 6. This indicates that the lysine carbon chain is cleaved between both carbon atoms 2 and 3 and carbon atoms 4 and 5, with the former predominating [1-14C]acetate was also extensively incorporated into butyrate, preferentially into carbon atoms 3 and 4. Cell-free extracts of F. nucleatum were shown to catalyze the reactions of the 3-keto,5-aminohexanoate pathway of lysine degradation, previously described in lysine-fermenting clostridia. The 3-keto,5-aminohexanoate cleavage enzyme was partially purified and shown to have properties much like those of the clostridial enzyme. We conclude that both the pathway and the enzymes of lysine degradation are similar in F. nucleatum and lysine-fermenting clostridia.

  Lysine被Fusobacterium nucleatum ATCC 25586发酵，形成约1摩尔的醋酸和丁酸。通过使用[1-14C]赖氨酸或[6-14C]赖氨酸，醋酸和丁酸被证明来自赖氨酸的两端，其中醋酸优先从碳原子1和2形成，而丁酸优先从碳原子3到6形成。这表明赖氨酸碳链在碳原子2和3以及碳原子4和5之间被切断，前者占主导地位。[1-14C]醋酸也被广泛地并入丁酸中，优先进入碳原子3和4。F. nucleatum的细胞提取物被证明能催化赖氨酸降解的3-酮，5-氨基己酸途径反应，该途径先前在降解赖氨酸的梭菌中已被描述。3-酮，5-氨基己酸裂解酶被部分纯化，并显示出与梭菌酶类似的性质。我们得出结论，赖氨酸降解的途径和酶在F. nucleatum和降解赖氨酸的梭菌中是相似的。
• Snake Venom L-Amino Acid Oxidases: Trends in Pharmacology and Biochemistry
  作者：Luiz Fernando M. Izidoro、Juliana C. Sobrinho、Mirian M. Mendes、Tássia R. Costa、Amy N. Grabner、Veridiana M. Rodrigues、Saulo L. da Silva、Fernando B. Zanchi、Juliana P. Zuliani、Carla F. C. Fernandes、Leonardo A. Calderon、Rodrigo G. Stábeli、Andreimar M. Soares

  DOI：10.1155/2014/196754

  日期：——

  L-amino acid oxidases are enzymes found in several organisms, including venoms of snakes, where they contribute to the toxicity of ophidian envenomation. Their toxicity is primarily due to enzymatic activity, but other mechanisms have been proposed recently which require further investigation. L-amino acid oxidases exert biological and pharmacological effects, including actions on platelet aggregation and the induction of apoptosis, hemorrhage, and cytotoxicity. These proteins present a high biotechnological potential for the development of antimicrobial, antitumor, and antiprotozoan agents. This review provides an overview of the biochemical properties and pharmacological effects of snake venom L-amino acid oxidases, their structure/activity relationship, and supposed mechanisms of action described so far.

  L-氨基酸氧化酶是一种酶，存在于多种生物体中，包括蛇毒中，其中它们对蛇毒的毒性起着贡献。它们的毒性主要是由于酶活性，但最近提出了其他机制，需要进一步研究。L-氨基酸氧化酶对血小板聚集和诱导凋亡、出血和细胞毒性等具有生物学和药理学作用。这些蛋白质具有高度的生物技术潜力，可用于开发抗微生物、抗肿瘤和抗原虫药物。本综述概述了蛇毒L-氨基酸氧化酶的生化特性和药理学效应，它们的结构/活性关系以及迄今为止所描述的假定作用机制。