Trt-Thr-OH * Et3N

• 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: Trt-Thr-OH * Et3N
• 英文别名: triethylammonium N-trityl-L-threonine；Trt-L-thr-OH tea；N,N-diethylethanamine;(2S,3R)-3-hydroxy-2-(tritylamino)butanoic acid
• 化学式: C₆H₁₅N*C₂₃H₂₃NO₃
• 分子量: 462.632
• InChiKey: LBHFGPKGFSTBMH-JKSHRDEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  72.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Trt-Thr-OH * Et3N 在 Pd-BaSO₄ 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 79.67h， 生成 (2S,3S)-1-trityl-3-methyl-2-aziridinecarboxylic acid
  参考文献：
  名称：

  Aziridine-2-carboxylic Acid-Containing Peptides:  Application to Solution- and Solid-Phase Convergent Site-Selective Peptide Modification

  摘要：

  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.

  DOI：

  10.1021/ja050304r

文献信息

• Darstellung und einsatz von N-Fmoc-O-Trt-hydroxyaminosäuren zur “solid phase” synthese von peptiden
  作者：Kleomenis Barlos、Dimitrios Gatos、Sophia Koutsogianni、Wolfram Schäfer、George Stavropoulos、Yao Wenging

  DOI：10.1016/s0040-4039(00)79471-8

  日期：1991.1

  The preparation of the N-Fmoc-O-Trt derivatives of serine, threonine and tyrosine is described. Their usefulness in peptide synthesis has been determined in the successful solid phase preparation of the partially protected ACTH (fragment 1-10) and peptide T 12. The latter, having six hydroxy amino acid side chains protected with Trt groups, can be quantitatively cleaved from the applied 2-chlorotrityl resin with simultaneous side chain deprotection.
• 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.