(R)-propyl aziridine-2-carboxylate | 1000072-76-3

• 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: (R)-propyl aziridine-2-carboxylate
• 英文别名: propyl (R)-aziridine-2-carboxylate；propyl (2R)-aziridine-2-carboxylate
• CAS: 1000072-76-3
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: YEPCVIBNQHROMW-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-propyl aziridine-2-carboxylate 在 二异丁基氢化铝 、 甲醇 作用下， 以 甲苯 、 噻吩 为溶剂， 以57%的产率得到2-aziridin-2-yl-3-oxa-1-aza-bicyclo[3.1.0]hexan-4-ol
  参考文献：
  名称：

  Chemoselective Peptidomimetic Ligation Using Thioacid Peptides and Aziridine Templates

  摘要：

  Chemoselective peptidomimetic ligation has been made possible using thioacid peptides and NH aziridine-terminated amino acids and peptides. In the course of this reaction, a reduced amide bond is incorporated into the backbone of a peptide. This process enables incorporation of reduced cysteine, reduced substituted cysteine, reduced phenylalanine, and reduced alanine. Our method should be adaptable to other unnatural amino acid residues at the ligation site. Experiments aimed at evaluating the chemoselectivity of this process in the presence of competing thiol nucleophiles suggest high specificity at micromolar concentrations. This holds even in the presence of glutathione, which neutralizes xenobiotic electrophiles in cells.

  DOI：

  10.1021/ja104488d
• 作为产物：
  描述：

  O-丙基-D-丝氨酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-propyl aziridine-2-carboxylate
  参考文献：
  名称：

  Chemoselective Peptidomimetic Ligation Using Thioacid Peptides and Aziridine Templates

  摘要：

  Chemoselective peptidomimetic ligation has been made possible using thioacid peptides and NH aziridine-terminated amino acids and peptides. In the course of this reaction, a reduced amide bond is incorporated into the backbone of a peptide. This process enables incorporation of reduced cysteine, reduced substituted cysteine, reduced phenylalanine, and reduced alanine. Our method should be adaptable to other unnatural amino acid residues at the ligation site. Experiments aimed at evaluating the chemoselectivity of this process in the presence of competing thiol nucleophiles suggest high specificity at micromolar concentrations. This holds even in the presence of glutathione, which neutralizes xenobiotic electrophiles in cells.

  DOI：

  10.1021/ja104488d

文献信息

• AZIRIDINE ALDEHYDES, AZIRIDINE-CONJUGATED AMINO DERIVATIVES, AZIRIDINE-CONJUGATED BIOMOLECULES AND PROCESSES FOR THEIR PREPARATION
  申请人：Yudin Andrei K.

  公开号：US20100317832A1

  公开（公告）日：2010-12-16

  The present invention applications for same. More particularly, the present invention relates to novel aziridine aldehydes and processes for preparing these novel compounds. The invention also relates to aziridine-conjugated amino derivatives, and processes for preparing the same. Pentacyclic compounds may be prepared using the aziridine aldehydes of the present invention, and the invention relates to these compounds and the processes by which they are made. The invention also relates to aziridine-conjugated bioactive molecules, such as amino acids and peptides, and processes for preparing such compounds.

  本发明适用于同类领域。更具体地说，本发明涉及新型环氧丙烷醛和制备这些新化合物的方法。本发明还涉及环氧丙烷醛偶联的氨基衍生物以及制备它们的方法。可以使用本发明的环氧丙烷醛制备五环化合物，并且本发明涉及这些化合物以及制备它们的方法。本发明还涉及环氧丙烷醛偶联的生物活性分子，例如氨基酸和肽，以及制备这些化合物的方法。
• WO2008/46232
  申请人：——

  公开号：——

  公开（公告）日：——
• Epimerization- and Protecting-Group-Free Synthesis of Peptidomimetic Conjugates from Amphoteric Amino Aldehydes
  作者：Xinghan Li、Andrei K. Yudin

  DOI：10.1021/ja076155p

  日期：2007.11.1

  We have developed a novel protecting-group-free strategy for the synthesis of peptidomimetic conjugates. The high degrees of stereocontrol and chemoselectivity achieved in this chemistry hinge upon unusual preferences of the amphoteric amino aldehydes. The resulting conjugates contain reduced amide bonds at defined positions, offering a possibility for peptidomimetic ligation. These findings should allow access to templates for introducing both natural and unnatural amino acid residues in close proximity to the reduced amide bond isosteres.
• US8143375B2
  申请人：——

  公开号：US8143375B2

  公开（公告）日：2012-03-27
• Chemoselective Peptidomimetic Ligation Using Thioacid Peptides and Aziridine Templates
  作者：Naila Assem、Aditya Natarajan、Andrei K. Yudin

  DOI：10.1021/ja104488d

  日期：2010.8.18

  Chemoselective peptidomimetic ligation has been made possible using thioacid peptides and NH aziridine-terminated amino acids and peptides. In the course of this reaction, a reduced amide bond is incorporated into the backbone of a peptide. This process enables incorporation of reduced cysteine, reduced substituted cysteine, reduced phenylalanine, and reduced alanine. Our method should be adaptable to other unnatural amino acid residues at the ligation site. Experiments aimed at evaluating the chemoselectivity of this process in the presence of competing thiol nucleophiles suggest high specificity at micromolar concentrations. This holds even in the presence of glutathione, which neutralizes xenobiotic electrophiles in cells.