{(S)-5-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-pentanoylamino}-acetic acid (benzhydryl-carbamoyl)-methyl ester | 209269-83-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: {(S)-5-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-pentanoylamino}-acetic acid (benzhydryl-carbamoyl)-methyl ester
• 英文别名: Boc-Tyr-Orn(Cbz)-Gly-OGly-NHbenzhydryl；[2-(benzhydrylamino)-2-oxoethyl] 2-[[(2S)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-5-(phenylmethoxycarbonylamino)pentanoyl]amino]acetate
• CAS: 209269-83-0
• 化学式: C₄₄H₅₁N₅O₁₀
• 分子量: 809.916
• InChiKey: AEJIHGISFZGTQT-ZPGRZCPFSA-N

物化性质

• 沸点：
  1068.017±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.247±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  59
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  211
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  {(S)-5-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-pentanoylamino}-acetic acid (benzhydryl-carbamoyl)-methyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-{(S)-4-{[(Benzhydryl-carbamoyl)-methoxycarbonylmethyl]-carbamoyl}-4-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-butylcarbamoyl}-butyric acid
  参考文献：
  名称：

  Modification of receptor selectivity and functional activity of cyclic cholecystokinin analogues

  摘要：

  We reported earlier on the synthesis and biological activity at the CCK-B receptor of cyclized derivatives of CCK. These peptides, in which the positions 28 and 31 were replaced by lysine residues, were bridged by a succinyl moiety. To determine the importance Of the nature and size of the cyclic structure, cyclic analogues were synthesized in which: (i) the lysine residues were replaced by ornithine and diaminobutyric acid and (ii) the succinic moiety was replaced by a malonic, adipic and glutaric moiety. They were tested for their ability to inhibit the specific binding of I-125-BH-CCK-8 to CCK receptors in rat pancreatic acini and guinea pig brain membranes. They were also evaluated for their ability to stimulate amylase secretion from rat pancreatic acini. The potency and selectivity of these analogues were compared with those obtained with CCK-4 and compound JMV320, a potent and selective CCK-B receptor ligand synthesized earlier in our laboratory. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80006-8
• 作为产物：
  描述：

  N-叔丁氧羰基-N'-苄氧羰基-L-鸟氨酸 在 N-甲基吗啉 、 N,N-二异丙基乙胺 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 反应 2.08h， 生成 {(S)-5-Benzyloxycarbonylamino-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-pentanoylamino}-acetic acid (benzhydryl-carbamoyl)-methyl ester
  参考文献：
  名称：

  Modification of receptor selectivity and functional activity of cyclic cholecystokinin analogues

  摘要：

  We reported earlier on the synthesis and biological activity at the CCK-B receptor of cyclized derivatives of CCK. These peptides, in which the positions 28 and 31 were replaced by lysine residues, were bridged by a succinyl moiety. To determine the importance Of the nature and size of the cyclic structure, cyclic analogues were synthesized in which: (i) the lysine residues were replaced by ornithine and diaminobutyric acid and (ii) the succinic moiety was replaced by a malonic, adipic and glutaric moiety. They were tested for their ability to inhibit the specific binding of I-125-BH-CCK-8 to CCK receptors in rat pancreatic acini and guinea pig brain membranes. They were also evaluated for their ability to stimulate amylase secretion from rat pancreatic acini. The potency and selectivity of these analogues were compared with those obtained with CCK-4 and compound JMV320, a potent and selective CCK-B receptor ligand synthesized earlier in our laboratory. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80006-8