N-tert-butoxycarbonyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycine ethyl ester | 398461-05-7

• 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-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycine ethyl ester
• CAS: 398461-05-7
• 化学式: C₇₀H₈₉N₉O₁₅
• 分子量: 1296.53
• InChiKey: DLMQDVQCXYVLSX-FISOEBTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  94.0
• 可旋转键数：
  37.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  303.82
• 氢给体数：
  6.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycine ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 ε-(3-hydroxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-hydroxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-hydroxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycine ethyl ester TFA salt
  参考文献：
  名称：

  3-Hydroxy-4(1H)-pyridinone-containing Linear and Cyclic Hexapeptides and Their Iron(III) Complexes —Synthesis, Property, and the Growth-Promotion Activity —

  摘要：

  Linear and cyclic hexapeptides composed of epsilon-(3-hydroxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L,norleucine and glycine or P-alanine residue have been successfully synthesized. These hexapeptides formed 1:1 iron(III) complexes at neutral pH region. Glycine linear (8a)- and beta -alanine cyclic hexapeptide (10)-iron(III) complexes predominantly existed in Delta -configuration, while P-alanine linear hexapeptide (8b)-iron(III) complex existed in Lambda -one. The relative stability constants of 8a, 8b, and 10-iron(III) complexes were estimated to be 31.6, 33.4, and 31.7, respectively. From iron(III) removal from human transferrin, linear hexapeptides (8a,b) were found to efficiently remove iron(III) compared with desferrioxamine B. The growth-promotion activity was also discussed.

  DOI：

  10.3987/com-01-9338
• 作为产物：
  描述：

  L-赖氨酸盐酸盐 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-羰基二咪唑 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 298.0h， 生成 N-tert-butoxycarbonyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycyl-ε-(3-benzyloxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L-norleucylglycine ethyl ester
  参考文献：
  名称：

  3-Hydroxy-4(1H)-pyridinone-containing Linear and Cyclic Hexapeptides and Their Iron(III) Complexes —Synthesis, Property, and the Growth-Promotion Activity —

  摘要：

  Linear and cyclic hexapeptides composed of epsilon-(3-hydroxy-1,4-dihydro-2-methyl-4-oxo-1-pyridyl)-L,norleucine and glycine or P-alanine residue have been successfully synthesized. These hexapeptides formed 1:1 iron(III) complexes at neutral pH region. Glycine linear (8a)- and beta -alanine cyclic hexapeptide (10)-iron(III) complexes predominantly existed in Delta -configuration, while P-alanine linear hexapeptide (8b)-iron(III) complex existed in Lambda -one. The relative stability constants of 8a, 8b, and 10-iron(III) complexes were estimated to be 31.6, 33.4, and 31.7, respectively. From iron(III) removal from human transferrin, linear hexapeptides (8a,b) were found to efficiently remove iron(III) compared with desferrioxamine B. The growth-promotion activity was also discussed.

  DOI：

  10.3987/com-01-9338