(2S,3S)-1-trityl-3-methyl-2-aziridinecarboxylic acid | 74481-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2S,3S)-1-trityl-3-methyl-2-aziridinecarboxylic acid
• 英文别名: (2S,3S)-3-methyl-1-tritylaziridine-2-carboxylic acid；(2S,3S)-1-Tri-3-methyl-2-aziridinecarboxylic acid；Trt-(3-Me-Azy)-OH；TrtAzy(3-Me)OH
• CAS: 74481-57-5
• 化学式: C₂₃H₂₁NO₂
• 分子量: 343.425
• InChiKey: HUPXHRVMFVVBCY-PJJDVYEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-phenylalanine benzylamide 、 (2S,3S)-1-trityl-3-methyl-2-aziridinecarboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 以72%的产率得到(2S,3S)-3-Methyl-1-trityl-aziridine-2-carboxylic acid ((S)-1-benzylcarbamoyl-2-phenyl-ethyl)-amide
  参考文献：
  名称：

  Conjugation of Selenols with Aziridine-2-Carboxylic Acid-Containing Peptides

  摘要：

  描述了在含有氮丙啶-2-羧酸的多肽中添加苯硒醇的过程，从而扩大了对于这类电亲核性多肽底物开环的亲核体范围。该过程提供了一种生成有用的苯硒半胱氨酸衍生物和含α-硒-β-氨基酸的多肽的新策略。

  DOI：

  10.1055/s-2005-871972
• 作为产物：
  描述：

  methyl (2S,3S)-N-triphenylmethyl-3-methylaziridine-2-carboxylate 在 lithium hydroxide 作用下， 生成 (2S,3S)-1-trityl-3-methyl-2-aziridinecarboxylic acid
  参考文献：
  名称：

  通过氮丙啶†的开环反应进行放线菌素D（C 1）的全合成

  摘要：

  放线菌素D（C 1）已通过涉及两个肽片段（2 S，3 S）-1-（2-硝基-3-苄氧基-4-甲基苯甲酰基）-3-甲基-2之间酯形成的途径合成-氮丙啶-羰基-D-戊基脯氨酸叔丁酯和N-苄氧基羰基肌氨酸-N-甲基缬氨酸，通过氮丙啶的开环反应。环化，然后还原和氧化，得到放线菌素D（C 1）。就物理性质和生物活性而言，合成放线菌素D（C 1）与天然物质没有区别。

  DOI：

  10.1002/jhet.5570170840

文献信息

• Aziridine-Mediated Ligation and Site-Specific Modification of Unprotected Peptides
  作者：Frank Brock Dyer、Chung-Min Park、Ryan Joseph、Philip Garner

  DOI：10.1021/ja207133t

  日期：2011.12.21

  ligation site. The aziridine-mediated peptide ligation concept is exemplified using H(2)O as the nucleophile, producing a Xaa-Thr linkage (where Xaa can be an epimerizable and hindered amino acid). The overall process is compatible with a variety of unprotected amino acid functionality, most notably the N-terminal and Lys side chain amines.

  报道了通过未保护的肽硫代酸和 NH 氮丙啶-2-羰基肽的 Cu(II) 促进偶联合成含氮丙啶肽。所得 N-酰化氮丙啶-2-羰基肽的独特反应性促进了它们随后的区域选择性和立体选择性亲核开环，以产生在连接位点被特异性修饰的未保护肽。氮丙啶介导的肽连接概念以 H(2)O 作为亲核试剂为例，产生 Xaa-Thr 连接（其中 Xaa 可以是差向异构和受阻氨基酸）。整个过程与各种未受保护的氨基酸官能团兼容，最显着的是 N 端和 Lys 侧链胺。
• [EN] HETEROCYCLIC AMINO ACIDS<br/>[FR] ACIDES AMINÉS HÉTÉROCYCLIQUES
  申请人：BAYER PHARMA AG

  公开号：WO2011151348A1

  公开（公告）日：2011-12-08

  This invention relates to heterocyclic amino acid derivatives suitable for labeling or already labeled with 18F or 19F, methods of preparing such compounds, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for imaging proliferative diseases.

  该发明涉及适用于标记或已标记为18F或19F的杂环氨基酸衍生物，制备这种化合物的方法，包含这种化合物的组合物，包含这种化合物或组合物的试剂盒以及用于成像增殖性疾病的这种化合物、组合物或试剂盒的用途。
• [EN] CDK2 INHIBITORS AND METHODS OF USING THE SAME<br/>[FR] INHIBITEURS DE CDK2 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CEDILLA THERAPEUTICS INC

  公开号：WO2022165513A1

  公开（公告）日：2022-08-04

  The present disclosure provides compounds, compositions thereof, and methods of using the same for the inhibition of CDK2, and the treatment of CDK2 related diseases and disorders.

  本公开提供了抑制CDK2的化合物、其组合物以及使用它们治疗CDK2相关疾病和疾病的方法。
• A Versatile Scaffold for Site-Specific Modification of Cyclic Tetrapeptides
  作者：Christopher J. White、Andrei K. Yudin

  DOI：10.1021/ol301178r

  日期：2012.6.1

  A novel scaffold that can be used to prepare conformationally homogeneous cyclic tetrapeptides equipped with a beta-amino acid residue is disclosed. It Is shown that regioselective structural modification can be accomplished using thiols and azide nucleophiles, commonly associated with rich downstream chemistry. The method should find application in efforts to constrain privileged tripeptide sequences in rigid molecular scaffolds.
• Aziridine-2-carboxylic Acid-Containing Peptides:  Application to Solution- and Solid-Phase Convergent Site-Selective Peptide Modification
  作者：Danica P. Galonić、Nathan D. Ide、Wilfred A. van der Donk、David Y. Gin

  DOI：10.1021/ja050304r

  日期：2005.5.25

  The development of a method for site- and stereoselective peptide modification using aziridine2-carboxylic acid-containing peptides is described. A solid-phase peptide synthesis methodology that allows for the rapid generation of peptides incorporating the aziridine residue has been developed. The unique electrophilic nature of this nonproteinogenic amino acid allows for site-selective conjugation with various thiol nucleophiles, such as anomeric carbohydrate thiols, farnesyl thiol, and biochemical tags, both in solution and on solid support. This strategy, combined with native chemical ligation, provides convergent and rapid access to complex thioglycoconjugates.