ε-N-crotonyl lysine | 1399861-03-0

• 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: ε-N-crotonyl lysine
• 英文别名: N^ε-crotonyl-L-lysine；Lysine(crotonyl)-OH；(2S)-2-amino-6-[[(E)-but-2-enoyl]amino]hexanoic acid
• CAS: 1399861-03-0
• 化学式: C₁₀H₁₈N₂O₃
• 分子量: 214.265
• InChiKey: IZHPCCLNIDDVFG-NCJLJLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到ε-N-crotonyl lysine
  参考文献：
  名称：

  Synthesis of ε-N-propionyl-, ε-N-butyryl-, and ε-N-crotonyl-lysine containing histone H3 using the pyrrolysine system

  摘要：

  最近在组蛋白和其他蛋白质中检测到新的赖氨酸修饰。使用吡咯赖氨酸琥珀抑制系统，我们将三个新氨基酸 ε-N-丙酰-、ε-N-丁酰-和 ε-N-巴豆酰-赖氨酸位点特异性插入组蛋白 H3 中。已知染色质中高度修饰的第 9 位赖氨酸 (H3 K9) 被这些非天然氨基酸取代。

  DOI：

  10.1039/c2cc37836a

文献信息

• Creation of a Yeast Strain with Co‐Translationally Acylated Nucleosomes
  作者：Dan Wu、Yunfeng Zhang、Zhiheng Tang、Xiaoxu Chen、Xinyu Ling、Longtu Li、Wenbing Cao、Wei Zheng、Jiale Wu、Hongting Tang、Xiaoyun Liu、Xiaozhou Luo、Tao Liu

  DOI：10.1002/anie.202205570

  日期：2022.7.25

  An engineered yeast strain was created by replacing genomic histones with mutants using an optimized yeast genetic code expansion (GCE) system. It can survive with co-translationally modified nucleosomes at the H3K56 position, providing insight into the functional differences in lysine acylation states, which might otherwise be difficult to study. Phenotypic variation between lysine acetylation and

  通过使用优化的酵母遗传密码扩展 (GCE) 系统用突变体替换基因组组蛋白来创建工程酵母菌株。它可以在 H3K56 位置与共翻译修饰的核小体一起存活，从而深入了解赖氨酸酰化状态的功能差异，否则可能难以研究。在该菌株中观察到赖氨酸乙酰化和巴豆酰化之间的表型变异。
• Site-Specific Incorporation of ε-N-Crotonyllysine into Histones
  作者：Chan Hyuk Kim、Mingchao Kang、Hak Joong Kim、Abhishek Chatterjee、Peter G. Schultz

  DOI：10.1002/anie.201203349

  日期：2012.7.16

  A novel post-translationally modified amino acid, crotonyllysine (Kcr), was genetically incorporated into proteins in bacterial and mammalian cells using an evolved pyrrolysyl-tRNA/synthetase-tRNA pair. The ability to produce histones with homogenous, site-specific Kcr modifications will be valuable in elucidating the biological role of this recently identified post-translational modification.
• [EN] METHODS AND KITS FOR DETERMINING DEACYLASE ACTIVITY<br/>[FR] PROCÉDÉS ET KITS DE DÉTERMINATION D'UNE ACTIVITÉ DE DÉSACYLASE
  申请人：THE NAT INST FOR BIOTECHNOLOGY IN THE NEGEV LTD

  公开号：WO2017064718A1

  公开（公告）日：2017-04-20

  Methods and kits for determining deacylase activity on an acylated lysine residue of a target polypeptide are disclosed. The methods disclosed comprise: providing one or more bacterial cells comprising: (i) an orthogonal pair of tRNA synthetase and tRNA; and/or (ii) a polynucleotide sequence encoding a target polypeptide, wherein said polynucleotide sequence comprises at least one codon that is specifically recognized by said tRNA; and (iii) at least one mammalian deacetylase; incubating said bacterial cell or extract thereof in the presence of Nɛ-acetyl lysine, wherein said tRNA is aminoacylated with Nɛ-modified lysine and incorporates the Nɛ-modified lysine into said target polypeptide, thereby expressing said target polypeptide comprising an Nɛ-modified lysine residue; determining the acylation levels of said target polypeptide; and comparing said acylation levels to a control; thereby determining deacylase activity.
• Synthesis of ε-N-propionyl-, ε-N-butyryl-, and ε-N-crotonyl-lysine containing histone H3 using the pyrrolysine system
  作者：Michael J. Gattner、Milan Vrabel、Thomas Carell

  DOI：10.1039/c2cc37836a

  日期：——

  Recently new lysine modifications were detected in histones and other proteins. Using the pyrrolysine amber suppression system we genetically inserted three of the new amino acids ε-N-propionyl-, ε-N-butyryl-, and ε-N-crotonyl-lysine site specifically into histone H3. The lysine at position 9 (H3 K9), which is known to be highly modified in chromatin, was replaced by these unnatural amino acids.

  最近在组蛋白和其他蛋白质中检测到新的赖氨酸修饰。使用吡咯赖氨酸琥珀抑制系统，我们将三个新氨基酸 ε-N-丙酰-、ε-N-丁酰-和 ε-N-巴豆酰-赖氨酸位点特异性插入组蛋白 H3 中。已知染色质中高度修饰的第 9 位赖氨酸 (H3 K9) 被这些非天然氨基酸取代。