methyl {2-[(tert-butoxycarbonylamino)acetamido]prop-2-enamido}acetate | 73260-53-4

• 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: methyl {2-[(tert-butoxycarbonylamino)acetamido]prop-2-enamido}acetate
• 英文别名: Boc-Gly-ΔAla-Gly-OMe；tert-butoxycarbonylglycyl-dehydroalanyl-glycine methyl ester；methyl 2-[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]prop-2-enoylamino]acetate
• CAS: 73260-53-4
• 化学式: C₁₃H₂₁N₃O₆
• 分子量: 315.326
• InChiKey: XPSWAEAEYIAGNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Boc-Gly-ΔAla 在 1-羟基苯并三唑 作用下， 反应 24.0h， 生成 methyl {2-[(tert-butoxycarbonylamino)acetamido]prop-2-enamido}acetate
  参考文献：
  名称：

  Conformation oftert-butoxycarbonylglycyl-dehydroalanyl-glycine methyl ester in the crystalline state and calculated in the gas phase

  摘要：

  tert-Butoxycarbonylglycyl-dehydroalanyl-glycine methyl ester ( systematic name: methyl {2-[(tert-butoxycarbonylamino)acetamido] prop-2-enamido}acetate) (Boc(0)-Gly(1)-Delta Ala(2)-Gly(3)-OMe), C13H21N3O6, has been structurally characterized by single-crystal X- ray diffraction and by density functional theory (DFT) calculations at the B3LYP/6-311+G** level. The peptide chain in both the solid-state and calculated structures adopts neither beta nor gamma turns. All amino acid residues in the tripeptide sequence are linked trans to each other. The bond lengths and valence angles of the amino acid units in the crystal structure and gas phase are comparable. However, the conformation of the third glycyl residue (Gly(3)) is different in the crystalline state and in the gas phase. It is stabilized in the calculated structure by an additional intramolecular short contact between Gly(3) NH and methyl ester COMe groups.

  DOI：

  10.1107/s0108270106052590

文献信息

• Makowski, Maciej; Rzeszotarska, Barbara; Kubica, Zbigniew, Liebigs Annalen der Chemie, 1986, # 6, p. 980 - 991
  作者：Makowski, Maciej、Rzeszotarska, Barbara、Kubica, Zbigniew、Pietrzynski, Grzegorz、Hetper, Jacek

  DOI：——

  日期：——