甲基(2E)-3-(4-甲氧基苯基)丙烯酸酯 | 88492-29-9

• 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: 甲基(2E)-3-(4-甲氧基苯基)丙烯酸酯
• 中文别名: 2-[甲酰基(2-羟基乙基)氨基]乙基(9Z,12Z)-十八碳-9,12-二烯酸酯
• 英文名称: N^ε-Acetyl-N^ε-hydroxy-N^α-L-lysine
• 英文别名: N⁶-acetyl-N⁶-L-hydroxylysine；(2S)-6-[acetyl(hydroxy)amino]-2-azaniumylhexanoate
• CAS: 88492-29-9
• 化学式: C₈H₁₆N₂O₄
• 分子量: 204.226
• InChiKey: YXKGOSZASIKYPU-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲基(2E)-3-(4-甲氧基苯基)丙烯酸酯 在 sodium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.83h， 生成 N^α-NVOC-N^ε-acetyl-N^ε-hydroxy-O-(tert-butyl dimethylsilylethoxy ether)-L-lysine cyanomethyl ester
  参考文献：
  名称：

  Tetrahydrofuranyl and tetrahydropyranyl protection of amino acid side-chains enables synthesis of a hydroxamate-containing aminoacylated tRNA

  摘要：

  使用四氢呋喃基或四氢吡喃基的O保护，使含有羟酰胺的非天然氨基酸加入到抑制剂tRNA中，从而使氨基酸能够特异性地插入到转录因子TFIIIA中。

  DOI：

  10.1039/c4ob02212b
• 作为产物：
  描述：

  (S)-6-(Acetyl-benzoyloxy-amino)-2-benzyloxycarbonylamino-hexanoic acid tert-butyl ester 在 palladium on activated charcoal ammonium hydroxide 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.66h， 生成 甲基(2E)-3-(4-甲氧基苯基)丙烯酸酯
  参考文献：
  名称：

  氨基酸氧化。第五部分：由赖氨酸合成N 6-乙酰-N 6-羟基赖氨酸的新方法

  摘要：

  通过用过氧化苯甲酰氧化N 2-苄氧基羰基-L-赖氨酸叔丁酯中的氨基，并随后乙酰化，由L-赖氨酸合成N 6-乙酰基-N 6 -L-羟基赖氨酸。

  DOI：

  10.1016/s0040-4039(00)95430-3

文献信息

• Aerobactin biosynthesis and transport genes of plasmid ColV-K30 in Escherichia coli K-12
  作者：V de Lorenzo、A Bindereif、B H Paw、J B Neilands

  DOI：10.1128/jb.165.2.570-578.1986

  日期：1986.2

  The iron-regulated aerobactin operon, about 8 kilobase pairs in size, of the Escherichia coli plasmid ColV-K30 was shown by deletion and subcloning analyses to consist of at least five genes for synthesis (iuc, iron uptake chelate) and transport (iut, iron uptake transport) of the siderophore. The gene order iucABCD iutA was established. The genes were mapped within restriction nuclease fragments of a cloned 16.3-kilobase-pair HindIII fragment. Stepwise deletion and subsequent minicell analysis of the resulting plasmids allowed assignment of four of the five genes to polypeptides of molecular masses 63,000, 33,000 53,000, and 74,000 daltons, respectively. The 74-kilodalton protein, the product of gene iutA, is the outer membrane receptor for ferric aerobactin, whereas the remaining three proteins are involved in biosynthesis of aerobactin. The 33-kilodalton protein, the product of gene iucB, was identified as N epsilon-hydroxylysine:acetyl coenzyme A N epsilon-transacetylase (acetylase) by comparison of enzyme activity in extracts from various deletion mutants. The 53-kilodalton protein, the product of gene iucD, is required for oxygenation of lysine. The 63-kilodalton protein, the product of gene iucA, is assigned to the first step of the aerobactin synthetase reaction. The product of gene iucC, so far unidentified, performs the second and final step in this reaction. This is based on the chemical characterization of two precursor hydroxamic acids (N epsilon-acetyl-N epsilon-hydroxylysine and N alpha-citryl-N epsilon-acetyl-N epsilon-hydroxylysine) isolated from a strain carrying a 0.3-kilobase-pair deletion in the iucC gene. The results support the existence of a biosynthetic pathway in which aerobactin arises by oxygenation of lysine, acetylation of the N epsilon-hydroxy function, and condensation of 2 mol of the resulting aminohydroxamic acid with citric acid.

  大约8千碱基对大小的铁调节的氧合酶基因组，存在于大肠杆菌质粒ColV-K30中，通过缺失和亚克隆分析表明，该基因组至少由五个基因组成，用于合成（iuc，铁摄取螯合物）和运输（iut，铁摄取运输）铁载体。基因顺序为iucABCD iutA。这些基因位于克隆的16.3千碱基对HindIII片段的限制核酸酶片段内。逐步缺失和随后的微胞分析得出的质粒分配了其中四个基因到分子质量分别为63,000、33,000、53,000和74,000道尔顿的多肽中。74千道尔顿蛋白质，即iutA基因的产物，是铁摄取螯合物的外膜受体，而其余三个蛋白质则参与氧合酶的生物合成。33千道尔顿蛋白质，即iucB基因的产物，通过比较来自不同缺失突变体的提取物中的酶活性，被确定为Nε-羟基赖氨酸：乙酰辅酶A Nε-转乙酰酰化酶（乙酰化酶）。53千道尔顿蛋白质，即iucD基因的产物，需要氧化赖氨酸。63千道尔顿蛋白质，即iucA基因的产物，被分配到氧合酶合成酶反应的第一步。iucC基因的产物，到目前为止还没有确定，执行该反应的第二和最后一步。这是基于从携带iucC基因0.3千碱基对缺失的菌株中分离出的两个前体羟胺酸（Nε-乙酰-Nε-羟基赖氨酸和Nα-柠檬酸-Nε-乙酰-Nε-羟基赖氨酸）的化学表征。结果支持一种生物合成途径的存在，其中氧合酶通过氧化赖氨酸、Nε-羟基功能的乙酰化以及2摩尔的结果氨基羟肟酸与柠檬酸的缩合而产生。
• The long-overlooked enzymology of a nonribosomal peptide synthetase-independent pathway for virulence-conferring siderophore biosynthesis
  作者：Daniel Oves-Costales、Nadia Kadi、Gregory L. Challis

  DOI：10.1039/b913092f

  日期：——

  for siderophore biosynthesis exist in microbes. One pathway involves nonribosomal peptide synthetase (NRPS) multienzymes while the other is NRPS-independent. The enzymology of NRPS-mediated siderophore biosynthesis has been extensively studied for more than a decade. In contrast, the enzymology of NRPS-independent siderophore (NIS) biosynthesis was overlooked for almost thirty years since the first genetic

  铁载体是由大多数微生物生物合成和排泄的高亲和力三价铁螯合剂，在铁的获取中起重要作用。铁载体介导的从宿主中清除三价铁对病原微生物的毒力有显着影响。因此，铁载体生物合成是化疗干预的一个有吸引力的目标。微生物中存在两种主要的铁载体生物合成途径。一种途径涉及非核糖体肽合成酶 (NRPS) 多酶，而另一种途径不依赖于 NRPS。NRPS 介导的铁载体生物合成的酶学已被广泛研究了十多年。相比之下，自 NIS 生物合成途径到产氧菌素的首次遗传表征以来，NRPS 独立铁载体 (NIS) 生物合成的酶学被忽视了近 30 年。然而，在过去三年中，人们对 NIS 合成酶的酶学兴趣激增，NIS 合成酶是通过 NIS 途径组装铁载体的关键酶。自 2007 年以来，已经报道了 10 种纯化重组合成酶的生化表征，并在 2009 年首次通过 X 射线晶体学对合成酶进行了结构表征。在这篇专题文章中，我们总结了在理解长期被忽视的NRPS
• Characterization of iucA and iucC genes of the aerobactin system of plasmid ColV-K30 in Escherichia coli
  作者：V de Lorenzo、J B Neilands

  DOI：10.1128/jb.167.1.350-355.1986

  日期：1986.7

  A cloned 8.3-kilobase-pair DNA fragment carrying all the genes (iucABCD iutA) of the aerobactin iron transport system of plasmid pColV-K30 was subjected to in vitro mutagenesis to afford mutant genes iucA, iucC, and iucA iucC. Complementation analyses and identification of aerobactin precursors accumulated by Escherichia coli cells harboring the different constructions allowed assignment of the iucA and iucC genes to discrete steps in biosynthesis of the siderophore from N epsilon-acetyl-N epsilon-hydroxylysine and citrate. Plasmid pVLN10, a derivative carrying a DNA fragment complementing an iucC mutation, expressed in a minicell system a single 62,000-dalton protein as the product of this gene.

  对携带质粒pColV-K30的空气杆菌铁运输系统的所有基因（iucABCD iutA）的克隆8.3千碱基对DNA片段进行了体外突变，得到突变基因iucA、iucC和iucA iucC。通过补体分析和鉴定大肠杆菌细胞中积累的空气杆菌前体，可以将iucA和iucC基因分配到从Nε-乙酰基-Nε-羟基赖氨酸和柠檬酸合成铁载体的离散步骤中。质粒pVLN10是一个衍生物，携带一个补充iucC突变的DNA片段，在微小细胞系统中表达一个单一的62,000道尔顿蛋白作为该基因的产物。
• A New Method for the Synthesis ofN.epsilon.-Acetyl-N.epsilon.-hydroxy-L-lysine, the Iron-Binding Constituent of Several Important Siderophores
  作者：Jingdan Hu、Marvin J. Miller

  DOI：10.1021/jo00096a030

  日期：1994.8

  Oxidation of the
• Isolation and properties of N.epsilon.-hydroxylysine:acetyl coenzyme A N.epsilon.-transacetylase from Escherichia coli pABN11
  作者：Mark Coy、Barry H. Paw、Albrecht Bindereif、J. B. Neilands

  DOI：10.1021/bi00357a030

  日期：1986.5.1

  The enzyme N epsilon-hydroxylysine acetylase has been isolated from Escherichia coli 294 carrying recombinant plasmid ABN11. Activity of the enzyme was followed by measurement of the rate of appearance of 2-nitro-5-thiobenzoate, the product of cleavage of 5,5'-dithiobis(2-nitrobenzoate) by free coenzyme A released from its acetyl derivative. The enzyme bound firmly to Reactive Blue 2-Sepharose CL-6B and was eluated with 1.5 M KCl. The protein gave a single band, corresponding to a Mr of 33,000, on polyacrylamide gel electrophoresis in sodium dodecyl sulfate. In contrast, gel filtration of the native enzyme gave a Mr of 150,000-200,000. A sequence analysis of the DNA at the junction of the first and second genes in the aerobactin operon, considered in conjunction with the N-terminal amino acid sequence of the isolated protein, enabled the conclusion that the acetylase is specified by the second gene in the complex. The enzyme transfers the acetyl moiety from acetyl coenzyme A to a variety of hydroxylamines, with N epsilon-hydroxylysine as the preferred substrate. In agreement with the results found by affinity chromatography, Coomassie Blue was observed to act as a potent inhibitor.