N-trityl-L-threonine benzyl ester | 142941-65-9

• 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: N-trityl-L-threonine benzyl ester
• 英文别名: Trt-Thr-OBn；N-Trityl-D-threonine benzyl ester；benzyl (2S,3R)-3-hydroxy-2-(tritylamino)butanoate
• CAS: 142941-65-9
• 化学式: C₃₀H₂₉NO₃
• 分子量: 451.565
• InChiKey: WKJRVIJPNQQIHL-LXFBAYGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-trityl-L-threonine benzyl ester 在 甲酸 、 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.0h， 生成 benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate
  参考文献：
  名称：

  One-step synthesis of optically active benzyl N-trityl-L-aziridine-2-carboxylic esters

  摘要：

  Benzyl N-trityl-L-serine or threonine esters give upon treatment with sulphuryl chloride the corresponding benzyl (2S)-1-trityl-2-aziridine carboxylate or (2S, 3S)-1-trityl-3-methyl-2-aziridinecarboxylate esters in excellent yields.

  DOI：

  10.1016/s0040-4039(00)79586-4
• 作为产物：
  描述：

  溴甲苯 、 N-triphenylmethyl-(L)-threonine 以 四氢呋喃 为溶剂， 以80%的产率得到N-trityl-L-threonine benzyl ester
  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

文献信息

• 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.
• [EN] COMPOUNDS USEFUL IN THE TREATMENT OF ANTHRAX AND INHIBITING LETHAL FACTOR<br/>[FR] COMPOSES PERMETTANT DE TRAITER L'ANTHRAX ET D'INHIBER LE FACTEUR LETAL
  申请人：——

  公开号：WO2003101382A3

  公开（公告）日：2004-07-29
• Aziridine ring opening as regio- and stereoselective access to O-glycosyl amino acids and their transformation into O-glycopeptide mimetics
  作者：Andreas Schäfer、Dirk Henkensmeier、Lars Kröger、Joachim Thiem

  DOI：10.1016/j.tetasy.2009.02.038

  日期：2009.5

  Glycosyl amino acid mimetics of the typical GalNAc-(1 -> O)-Ser/Thr motif of O-glycopeptides were synthesised. Starting from galactose a 1,5-anhydro derivative could be obtained and regio- and stereoselectively coupled to serine- or threonine-derived aziridine compounds, respectively. The corresponding Fmoc derivatives could be used to prepare two 13-mer glycopeptides of the mucin MUC1 carrying instead of Ser-2 or Th-5, the corresponding O-glcycosyl amino acid mimetics. (C) 2009 Elsevier Ltd. All rights reserved.
• Conjugation of Selenols with Aziridine-2-Carboxylic Acid-Containing Peptides
  作者：David Y. Gin、Nathan D. Ide、Danica P. Galonić、Wilfred A. van der Donk

  DOI：10.1055/s-2005-871972

  日期：——

  The addition of PhSeH to aziridine-2-carboxylic acid containing peptides is described, thus expanding the scope of nucleophiles for the opening of this class of electrophilic peptide substrates. The process offers a new strategy for the generation of useful phenylselenocysteine derivatives and α-seleno-β-amino acid-containing peptides.

  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。
• One-step synthesis of optically active benzyl N-trityl-L-aziridine-2-carboxylic esters
  作者：E Kuyl-Yeheskiely、M Lodder、G.A van der Marel、J.H van Boom

  DOI：10.1016/s0040-4039(00)79586-4

  日期：1992.5

  Benzyl N-trityl-L-serine or threonine esters give upon treatment with sulphuryl chloride the corresponding benzyl (2S)-1-trityl-2-aziridine carboxylate or (2S, 3S)-1-trityl-3-methyl-2-aziridinecarboxylate esters in excellent yields.