Boc-Gly-(3-Me-Azy)-NHBn | 855258-16-1

• 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: Boc-Gly-(3-Me-Azy)-NHBn
• 英文别名: tert-butyl N-[2-[(2S,3S)-2-(benzylcarbamoyl)-3-methylaziridin-1-yl]-2-oxoethyl]carbamate
• CAS: 855258-16-1
• 化学式: C₁₈H₂₅N₃O₄
• 分子量: 347.414
• InChiKey: WOQKMQFZILYMRA-ADLLFZCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.51
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Boc-Gly-(3-Me-Azy)-NHBn 、 1-thio-2-N-acetylamino-3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-galactopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 18.0h， 以65%的产率得到Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[(1R,2R)-2-benzylcarbamoyl-2-(2-tert-butoxycarbonylamino-acetylamino)-1-methyl-ethylsulfanyl]-tetrahydro-pyran-4-yl ester
  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：

  Trt-Thr-NHBn 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 20.5h， 生成 Boc-Gly-(3-Me-Azy)-NHBn
  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