Fmoc-aziridine-2-carboxylic acid | 790692-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-aziridine-2-carboxylic acid
• 英文别名: Fmoc-Azy-OH；FmocAzyOH；(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)aziridine-2-carboxylic acid
• CAS: 790692-31-8
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: NDYOINYFNJSZQQ-UCFFOFKASA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  534.8±43.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-芴甲氧羰基-甘氨酰-甘氨酸 、 Fmoc-L-苯丙氨酸 、 乙酸酐 、 Fmoc-aziridine-2-carboxylic acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 Ac-Gly-Gly-Phe-Azy-Ala-OH
  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
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 aziridine-2-carboxylic acid lithium salt 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以85%的产率得到Fmoc-aziridine-2-carboxylic acid
  参考文献：
  名称：

  硫醇与含氮丙啶-2-羧酸肽的位点选择性偶联

  摘要：

  描述了含氮丙啶-2-羧酸的肽与硫醇在溶液和固体支持物上的合成和会聚位点选择性偶联。FmocAzyOH 在这种能力下的合成和使用证明了 Azy 部分在多步 Fmoc 固相肽合成 (SPPS) 中的有效掺入和耐受性，以及通过高度区域选择性碱基进行溶液和珠上连接的能力。促进氮丙啶开环过程。

  DOI：

  10.1021/ja046793x

文献信息

• 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。
• Structure elucidation and conformational analysis of gonadotropin releasing hormone and its novel synthetic analogue [Tyr(OMe)5, d-Lys6, Aze9NHEtGnRH: The importance of aromatic clustering in the receptor binding activity
  作者：J.M. Matsoukas、M Keramida、D Panagiotopoulos、T Mavromoustakos、H.L.S. Maia、G Bigam、D Pati、H.R. Habibi、G.J. Moore

  DOI：10.1016/s0223-5234(97)89637-7

  日期：1998.12
• Site-Selective Conjugation of Thiols with Aziridine-2-Carboxylic Acid-Containing Peptides
  作者：Danica P. Galonić、Wilfred A. van der Donk、David Y. Gin

  DOI：10.1021/ja046793x

  日期：2004.10.1

  The synthesis and convergent site-selective conjugation of aziridine-2-carboxylic acid-containing peptides with thiols, both in solution and on solid support, are described. The synthesis and use of FmocAzyOH in this capacity demonstrate both the efficient incorporation and tolerance of the Azy moiety in multistep Fmoc solid-phase peptide synthesis (SPPS), as well as the competence of solution and

  描述了含氮丙啶-2-羧酸的肽与硫醇在溶液和固体支持物上的合成和会聚位点选择性偶联。FmocAzyOH 在这种能力下的合成和使用证明了 Azy 部分在多步 Fmoc 固相肽合成 (SPPS) 中的有效掺入和耐受性，以及通过高度区域选择性碱基进行溶液和珠上连接的能力。促进氮丙啶开环过程。
• 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.