N-tert-butoxycarbonyl-(2S,3S)-β-mercapto-L-phenylalanine methyl ester | 949574-90-7

• 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-tert-butoxycarbonyl-(2S,3S)-β-mercapto-L-phenylalanine methyl ester
• 英文别名: Boc-(β-SH)-L-Phe-OMe；methyl (2R,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenyl-3-sulfanylpropanoate
• CAS: 949574-90-7
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: WQJSIYWHWBAIHG-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-(2S,3S)-β-mercapto-L-phenylalanine methyl ester 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以76%的产率得到N-叔丁氧羰基-L-苯丙氨酸甲酯
  参考文献：
  名称：

  Native Chemical Ligation at Phenylalanine

  摘要：

  Synthesis of erythro-N-Boc-beta-mercapto-L-phenylalanine enables native chemical ligation at phenylalanine. In the form of the S-ethyldisulfanyl derivative, the N-Boc amino acid is used to cap a tetrapeptide generated by Fmoc-SPPS. The native chemical ligation with C-terminal thioesters then occurs successfully and is followed by selective desulfurization of the benzylic C-S bond. The method is applied to the synthesis of LYRAMFRANK, thereby establishing compatibility with the reactive side chains and the ability to ligate other than glycine.

  DOI：

  10.1021/ja072804l
• 作为产物：
  描述：

  methyl (2R,3R)-3-(acetylthio)-2-((tert-butyloxycarbonyl)amino)-3-phenylpropionate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以0.65 g的产率得到N-tert-butoxycarbonyl-(2S,3S)-β-mercapto-L-phenylalanine methyl ester
  参考文献：
  名称：

  Native Chemical Ligation at Phenylalanine

  摘要：

  Synthesis of erythro-N-Boc-beta-mercapto-L-phenylalanine enables native chemical ligation at phenylalanine. In the form of the S-ethyldisulfanyl derivative, the N-Boc amino acid is used to cap a tetrapeptide generated by Fmoc-SPPS. The native chemical ligation with C-terminal thioesters then occurs successfully and is followed by selective desulfurization of the benzylic C-S bond. The method is applied to the synthesis of LYRAMFRANK, thereby establishing compatibility with the reactive side chains and the ability to ligate other than glycine.

  DOI：

  10.1021/ja072804l

文献信息

• METHODS FOR THE PREPARATION OF FUNCTIONALIZED PEPTIDES, PROTEINS AND CARBOHYDRATES AND THEIR CONJUGATES
  申请人：Crich David

  公开号：US20100222546A1

  公开（公告）日：2010-09-02

  The present invention relates to methods for ligation or derivatization of peptides, amino acids, and carbohydrates utilizing a chalcogen-based reactant, a peptide reactant, an amino acid reactant, a chalcogen-containing peptide reactant, a chalcogen-containing amino acid reactant, or a combination of two or more of the foregoing reactants substantially as described herein.
• Native Chemical Ligation at Phenylalanine
  作者：David Crich、Abhisek Banerjee

  DOI：10.1021/ja072804l

  日期：2007.8.1

  Synthesis of erythro-N-Boc-beta-mercapto-L-phenylalanine enables native chemical ligation at phenylalanine. In the form of the S-ethyldisulfanyl derivative, the N-Boc amino acid is used to cap a tetrapeptide generated by Fmoc-SPPS. The native chemical ligation with C-terminal thioesters then occurs successfully and is followed by selective desulfurization of the benzylic C-S bond. The method is applied to the synthesis of LYRAMFRANK, thereby establishing compatibility with the reactive side chains and the ability to ligate other than glycine.