benzyloxycarbonyl(O-sulfate)-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-β-L-phenylalanine amide | 85847-80-9

• 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: benzyloxycarbonyl(O-sulfate)-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-β-L-phenylalanine amide
• 英文别名: Cbz-Tyr(SO3H)-Met-Gly-Trp-Met-Asp(1)-OH.N(1)Phe-NH2；(2S)-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-2-[[(2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[[2-[[(2S)-4-methylsulfanyl-2-[[(2S)-2-(phenylmethoxycarbonylamino)-3-(4-sulfooxyphenyl)propanoyl]amino]butanoyl]amino]acetyl]amino]propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-oxobutanoic acid
• CAS: 85847-80-9
• 化学式: C₅₃H₆₃N₉O₁₅S₃
• 分子量: 1162.33
• InChiKey: DGFUIYJOXNTANV-WGXSSYHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  80
• 可旋转键数：
  33
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  432
• 氢给体数：
  11
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  (S)-2-{(S)-2-[(S)-2-(2-Amino-acetylamino)-3-(1H-indol-3-yl)-propionylamino]-4-methylsulfanyl-butyrylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid tert-butyl ester 在 pyridine-SO3 complex 、 茴香硫醚 、 1-羟基苯并三唑 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 benzyloxycarbonyl(O-sulfate)-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-β-L-phenylalanine amide
  参考文献：
  名称：

  Synthesis and some pharmacological properties of Z-Tyr(SO3H)-Met-Gly-Trp-Met-Asp(Phe-NH2)-OH, a 32-.beta.-aspartyl analog of cholecystokinin (pancreozymin)-27-33

  摘要：

  The heptapeptide carbobenzoxy-L-tyrosyl(O-sulfate)-L-methionylglycyl-L-tryptophyl-L-methionyl-L- aspartyl-beta-L-phenylalanine amine (Z-32-beta-Asp-CCK-27-33) was synthesized and tested for its ability to stimulate secretion from dispersed pancreatic acini in vitro, to increase protein secretion from cat pancreas in vivo, and to cause contraction of guinea pig gallbladder in situ. In increasing amylase secretion in vitro, the Z-32-beta-Asp-CCK-27-33 was equal in efficacy with but approximatively one-third as potent as the Boc-CCK-27-33, and when tested in vivo its activity is approximately 10 Ivy dog units (Idu)/microgram. In stimulation of the contraction of the gallbladder, it showed an activity lower than 1 Idu/microgram. This analogue has more pancreozyminic activity than cholecystokin-like activity. This seems to indicate different affinities for the two receptors.

  DOI：

  10.1021/jm00347a019

文献信息

• Synthesis and some pharmacological properties of Z-Tyr(SO3H)-Met-Gly-Trp-Met-Asp(Phe-NH2)-OH, a 32-.beta.-aspartyl analog of cholecystokinin (pancreozymin)-27-33
  作者：Jean Martinez、Francois Winternitz、Miklos Bodanszky、Jerry D. Gardner、Michael D. Walker、Victor Mutt

  DOI：10.1021/jm00347a019

  日期：1982.5

  The heptapeptide carbobenzoxy-L-tyrosyl(O-sulfate)-L-methionylglycyl-L-tryptophyl-L-methionyl-L- aspartyl-beta-L-phenylalanine amine (Z-32-beta-Asp-CCK-27-33) was synthesized and tested for its ability to stimulate secretion from dispersed pancreatic acini in vitro, to increase protein secretion from cat pancreas in vivo, and to cause contraction of guinea pig gallbladder in situ. In increasing amylase secretion in vitro, the Z-32-beta-Asp-CCK-27-33 was equal in efficacy with but approximatively one-third as potent as the Boc-CCK-27-33, and when tested in vivo its activity is approximately 10 Ivy dog units (Idu)/microgram. In stimulation of the contraction of the gallbladder, it showed an activity lower than 1 Idu/microgram. This analogue has more pancreozyminic activity than cholecystokin-like activity. This seems to indicate different affinities for the two receptors.