4-chloro-L-lysine

• 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: 4-chloro-L-lysine
• 英文别名: (2S)-6-amino-2-azaniumyl-4-chlorohexanoate
• 化学式: C₆H₁₃ClN₂O₂
• 分子量: 180.634
• InChiKey: RARMVOFXKPZWMG-AKGZTFGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  11
• 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：
  89.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-L-lysine 在 halogenase BesD 作用下， 反应 0.08h， 生成 4-hydroxylysine
  参考文献：
  名称：

  BesC 通过底物触发和反应性二铁-过氧中间体启动 C-C 裂解

  摘要：

  BesC 催化4-氯-l-赖氨酸依赖铁和 O 2的裂解，形成 4-氯-l-烯丙基甘氨酸、甲醛和氨。该过程是生物合成途径的关键步骤，该途径产生末端炔烃氨基酸，可用作蛋白质标记的有用生物正交句柄。作为以血红素加氧酶样折叠和一组非常相似的配位体（最近称为 HDOs）为代表的新兴二铁酶家族的一员，BesC 进行一种不寻常的碳-碳裂解反应，这与由典型的双核铁酶催化的反应。在这里，我们表明 BesC 激活 O 2以底物门控方式生成二铁-过氧中间体。检查过氧中间体与一系列赖氨酸衍生物的反应性表明，BesC 通过 C4-H 键的裂解启动了这种独特的反应轨迹；该过程代表单个转换反应中的限速步骤。观察到的 BesC 反应性代表了双核铁酶的第一个例子，它利用二铁-过氧中间体能够切割 C-H 键作为其天然功能的一部分，从而避免形成更常见的高价中间体与底物单氧合。

  DOI：

  10.1021/jacs.1c11109
• 作为产物：
  描述：

  L-赖氨酸盐酸盐 在 ammonium iron(II) sulfate hexahydrate 、 氧气 、 HalA from P_. fluorescens 、 sodium α-ketoglutarate 、 sodium ascorbate 、 sodium chloride 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 生成 4-chloro-L-lysine
  参考文献：
  名称：

  [EN] METHODS FOR SELECTIVELY MODIFYING AMINO ACIDS AND PRODUCTS MADE THEREBY
  [FR] PROCÉDÉS DE MODIFICATION SÉLECTIVE D'ACIDES AMINÉS ET PRODUITS FABRIQUÉS PAR CEUX-CI

  摘要：

  本文披露了一种选择性替代化合物中与碳原子结合的氢（例如，脂肪族亚甲基基团的氢）的方法，包括在BesD卤素酶存在的情况下将化合物与取代基接触。

  公开号：

  WO2021007127A1

文献信息

• LYSINE COMPOUNDS AND THEIR USE IN SITE- AND CHEMOSELECTIVE MODIFICATION OF PEPTIDES AND PROTEINS
  申请人：Ovaa Huib

  公开号：US20120135913A1

  公开（公告）日：2012-05-31

  The present invention concerns new thiolysine and selenolysine compounds that can be used as building blocks for peptides and proteins, providing ligation handles for site- and chemoselective modification of said peptides and proteins. In particular, the invention provides. In particular, the invention provides (the use of) the compounds 5-thiolysine (also referred to as δ-thiolysine); 4-thiolysine (also referred to as γ-thiolysine); 5-selenolysine (also referred to as δ-selenolysine) and 4-selenolysine (also referred to as γ-selenolysine). The positioning of the thiol or selenol group at the respective carbon atom allows for a very efficient intramolecular transfer reaction to take place after conjugation with a selected ligand, and the thiol or selenol group may subsequently be removed using reported procedures, thereby restoring the native lysine structure, or be used as an additional conjugation handle. The methodology is fast and gives well-defined material.

  本发明涉及新的巯基赖氨酸和硒基赖氨酸化合物，可用作肽和蛋白质的构建块，为所述肽和蛋白质的位点和化学选择性修饰提供连接手柄。具体而言，本发明提供了化合物5-巯基赖氨酸（也称为δ-巯基赖氨酸）；4-巯基赖氨酸（也称为γ-巯基赖氨酸）；5-硒基赖氨酸（也称为δ-硒基赖氨酸）和4-硒基赖氨酸（也称为γ-硒基赖氨酸）的使用。将巯基或硒基团位于相应的碳原子上，可在与所选配体共轭后发生非常高效的分子内转移反应，巯基或硒基团随后可使用已知的程序去除，从而恢复天然的赖氨酸结构，或用作额外的连接手柄。该方法快速且给出明确的材料。
• Reactions in Strong Acids. II.¹ New Concept in Amino Acid Chemistry: C-Derivatization of Amino Acids²
  作者：J. Kollonitsch、A. Rosegay、G. Doldouras

  DOI：10.1021/ja01063a045

  日期：1964.5.5
• TOTAL CHEMICAL SYNTHESIS OF UBIQUITIN, UBIQUITIN MUTANTS AND DERIVATIVES THEREOF
  申请人：Ovaa Huib

  公开号：US20130267680A1

  公开（公告）日：2013-10-10

  The present invention relates to the field of total chemical synthesis of ubiquitin and related peptides. More in particular, a method is provided of solid phase synthesis of ubiquitin, ubiquitin mutants and derivatives thereof. It was the object of the present invention to provide an approach for the total chemical synthesis of ubuiqitin, which allows for the chemical synthesis of virtually any Ub mutant and giving high overall efficiency and purity. The present inventors have surprisingly found that this object can be realized with a method relying on incorporation of special amino acid building blocks. This approach was found to allow for exceptionally high yields of up to 14% and to provide an synthetic entry into virtually any ubiquitin derivative.
• US8729009B2
  申请人：——

  公开号：US8729009B2

  公开（公告）日：2014-05-20
• [EN] LYSINE COMPOUNDS AND THEIR USE IN SITE- AND CHEMOSELECTIVE MODIFICATION OF PEPTIDES AND PROTEINS<br/>[FR] COMPOSÉS LYSINES ET LEUR UTILISATION DANS UNE MODIFICATION SÉLECTIVE DE SITE ET CHIMIOSÉLECTIVE DE PEPTIDES ET PROTÉINES
  申请人：STICHTING HET NL KANKER I

  公开号：WO2010131962A2

  公开（公告）日：2010-11-18

  The present invention concerns new thiolysine and selenolysine compounds that can be used as building blocks for peptides and proteins, providing ligation handles for site-and chemoselective modification of said peptides and proteins. In particular, the invention provides. In particular, the invention provides (the use of) the compounds 5-thiolysine (also referred to as δ-thiolysine); 4-thiolysine (also referred to as γ-thiolysine); 5-selenolysine (also referred to as δ-selenolysine) and 4- selenolysine (also referred to as γ-selenolysine). The positioning of the thiol or selenol group at the respective carbon atom allows for a very efficient intramolecular transfer reaction to take place after conjugation with a selected ligand, and the thiol or selenol group may subsequently be removed using reported procedures, thereby restoring the native lysine structure, or be used as an additional conjugation handle. The methodology is fast and gives well-defined material.