N-(tert-butoxycarbonyl)glycyl-L-leucyl-L-phenylalanine | 58173-07-2

• 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)glycyl-L-leucyl-L-phenylalanine
• 英文别名: Boc-Gly-Leu-Phe；N-(tert-Butoxycarbonyl)glycyl-L-leucyl-L-phenylalanine；(2S)-2-[[(2S)-4-methyl-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]pentanoyl]amino]-3-phenylpropanoic acid
• CAS: 58173-07-2
• 化学式: C₂₂H₃₃N₃O₆
• 分子量: 435.521
• InChiKey: WROIPIOIXIJSGP-IRXDYDNUSA-N

物化性质

• 沸点：
  700.2±60.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)glycyl-L-leucyl-L-phenylalanine 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 4.17h， 以93%的产率得到glycyl-L-leucyl-L-phenylalanine hydrochloride
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 2,2′-Azopyridine-Labeled Amines, Amino Acids, and Peptides

  摘要：

  A microwave-assisted procedure for labeling amines, amino acids, and peptides with 2,2'-azopyridines (2,2'-AzPy) is described using the corresponding 2,2'-azopyridine-diacylbenzotriazoles. The efficiency of the procedure is proven by the generation of three constitutionally isomeric sets of 2,2'-AzPy-X,X'-labeled amino conjugates (where X = 4, 5, 6) including amines, amino acids, and peptides. Microwave- assisted synthesis conditions provide good to excellent yields in less than 15 minutes with retention of original chirality. A trans-to-cis isomerization of the 2,2'-azopyridine-labeled amino conjugate upon laser irradiation at 325 nm is visualized with UV and NMR spectroscopy.

  DOI：

  10.1055/s-0035-1560523
• 作为产物：
  描述：

  N-[叔丁氧羰基]甘氨酰-L-亮氨酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 20.25h， 生成 N-(tert-butoxycarbonyl)glycyl-L-leucyl-L-phenylalanine
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 2,2′-Azopyridine-Labeled Amines, Amino Acids, and Peptides

  摘要：

  A microwave-assisted procedure for labeling amines, amino acids, and peptides with 2,2'-azopyridines (2,2'-AzPy) is described using the corresponding 2,2'-azopyridine-diacylbenzotriazoles. The efficiency of the procedure is proven by the generation of three constitutionally isomeric sets of 2,2'-AzPy-X,X'-labeled amino conjugates (where X = 4, 5, 6) including amines, amino acids, and peptides. Microwave- assisted synthesis conditions provide good to excellent yields in less than 15 minutes with retention of original chirality. A trans-to-cis isomerization of the 2,2'-azopyridine-labeled amino conjugate upon laser irradiation at 325 nm is visualized with UV and NMR spectroscopy.

  DOI：

  10.1055/s-0035-1560523

文献信息

• Microwave-Assisted Synthesis of 2,2′-Azopyridine-Labeled Amines, Amino Acids, and Peptides
  作者：Ilker Avan

  DOI：10.1055/s-0035-1560523

  日期：——

  A microwave-assisted procedure for labeling amines, amino acids, and peptides with 2,2'-azopyridines (2,2'-AzPy) is described using the corresponding 2,2'-azopyridine-diacylbenzotriazoles. The efficiency of the procedure is proven by the generation of three constitutionally isomeric sets of 2,2'-AzPy-X,X'-labeled amino conjugates (where X = 4, 5, 6) including amines, amino acids, and peptides. Microwave- assisted synthesis conditions provide good to excellent yields in less than 15 minutes with retention of original chirality. A trans-to-cis isomerization of the 2,2'-azopyridine-labeled amino conjugate upon laser irradiation at 325 nm is visualized with UV and NMR spectroscopy.