N^α-(tert-butyloxycarbonyl)-(R)-lysine tert-butyl ester

• 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-(tert-butyloxycarbonyl)-(R)-lysine tert-butyl ester
• 英文别名: Boc-t-Bu-lysine；Boc-Lys-OtBu；N(α)-(1,1-dimethylethoxycarbonyl)-L-lysine-tert-butryl ester；Boc-D-Lys-OtBu；tert-butyl (2R)-6-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• 化学式: C₁₅H₃₀N₂O₄
• 分子量: 302.414
• InChiKey: LVUBESNUUMLEHL-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^α-(tert-butyloxycarbonyl)-(R)-lysine tert-butyl ester 在 吡啶 、 N,N'-二琥珀酰亚胺基碳酸酯 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  一种含氟非天然赖氨酸衍生物的通用合成方 法

  摘要：

  本发明属于化学合成技术领域，具体为一种含氟非天然赖氨酸衍生物的通用合成方法。本发明首先将含氟醇类化合物ROH和DSC在碱作用下，在30‑50℃的温度下，在溶剂中反应，反应结束后，将混合物冷却至室温，加入Boc‑t‑Bu‑赖氨酸，继续室温下搅拌反应，反应结束后后处理得到含氟赖氨酸衍生物前体；然后将前体在TFA的CH2Cl2溶液中进行Boc和t‑Bu的脱保护，得到目标化合物。本发明方法以赖氨酸衍生物及含氟醇类化合物为原料合成了一系列含氟非天然赖氨酸，扩展了现有非天然赖氨酸衍生物的种类，为氟标记氨基酸的制备提供了新的合成方法。本发明具有简短高效、反应条件温和、环境友好、总收率高等优点。

  公开号：

  CN108997168B

文献信息

• [EN] METHODS OF PREPARING N6-((2-AZIDOETHOXY)CARBONYL)LYSINE<br/>[FR] PROCÉDÉS DE PRÉPARATION DE N6-((2-AZIDOÉTHOXY)CARBONYL)LYSINE
  申请人：SYNTHORX INC

  公开号：WO2021133839A1

  公开（公告）日：2021-07-01

  Disclosed herein are methods of preparing N6-((2-azidoethoxy)carbonyl)lysine, N6-((2-azidoethoxy)carbonyl)-L-lysine, and N6-((2-azidoethoxy)carbonyl)-D-lysine. Also disclosed herein are the compounds tert-butyl N2-(tert-butoxycarbonyl)-N6-((2-chloroethoxy)carbonyl)-L-lysinate and tertbutyl N6-((2-azidoethoxy)carbonyl)-N2-(tert-butoxycarbonyl)-L-lysinate, and uses thereof.

  本文披露了制备N6-((2-叠氮乙氧基)羰基)赖氨酸、N6-((2-叠氮乙氧基)羰基)-L-赖氨酸和N6-((2-叠氮乙氧基)羰基)-D-赖氨酸的方法。还披露了化合物叔丁基N2-(叔丁氧羰基)-N6-((2-氯乙氧基)羰基)-L-赖氨酸酯和叔丁基N6-((2-叠氮乙氧基)羰基)-N2-(叔丁氧羰基)-L-赖氨酸酯及其用途。
• Efficient Syntheses of a Flavin and an 8-Hydroxy-5-deazaflavin Amino Acid and Their Incorporation into Oligopeptides
  作者：Thomas Carell、Holger Schmid、Markus Reinhard

  DOI：10.1021/jo980643l

  日期：1998.11.1

  We report a convenient synthesis for the cofactor amino acids (S)-3 and (S)-4 in which the C-5-ribose chain of the original riboflavin and ribo-5-deazaflavin cofactors is replaced by a C-5-amino acid side chain. Both cofactor amino acids are available in enantiomerically pure form in gram quantities and can be incorporated into oligopeptides using a standard Fmoc-based solid-phase peptide synthesis protocol. The benzyl-protecting group of the 8-hydroxy-5-deazaflavin can be cleaved by hydrogenolysis directly on the peptide. This allows the investigation of the properties of the peptide bound redox active OH- and the deprotonated O--form of the deazaflavin. Due to the electron- and energy-transfer properties of both cofactors, applications of both amino acid in the preparation of peptide- and protein-based biosensors, of catalytically active peptides, or as chemical rulers for distance measurements in biopolymers based on the fluorescence resonance energy-transfer technology can be envisaged.
• Synthesis of the unnatural amino acid Nα-Nε-(ferrocene-1-acetyl)-l-lysine: A novel organometallic nuclease
  作者：Amanda M. Gellett、Paul W. Huber、Pamela J. Higgins

  DOI：10.1016/j.jorganchem.2008.06.012

  日期：2008.9

  The synthesis of a new unnatural amino acid, N-alpha-N-epsilon-(ferrocene-1-acetyl)-L-lysine, was achieved by coupling a ferroceneacetic acid molecule onto the side chain amine of a lysine. The structure of the compound provides options for incorporation of the molecule into peptides or large proteins. In addition, N-alpha-N-epsilon-(ferrocene-1-acetyl)-L-lysine exhibits nuclease activity. It is expected that incorporation of this ferrocenyl amino acid into any nucleic acid-binding protein will endow the protein with nuclease capability. (C) 2008 Elsevier B. V. All rights reserved.
• VHH ANTIBODY DOTA CONJUGATES
  申请人：[en]ABDERA THERAPEUTICS INC.

  公开号：WO2024044552A1

  公开（公告）日：2024-02-29

  Described herein are immunoconjugates comprising an: a) antigen binding region; b) an immunoglobulin heavy chain constant region; and c) a radioisotope chelating agent; wherein the molecular weight of said immunoconjugate is between 60 and 110 kDa. The immunoconjugates can be used to deliver alpha and beta emitters for the treatment of tumors or cancer.