(S)-3,4-二氨基-4-氧代-丁酸叔丁酯单盐酸盐 | 92786-68-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 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
• 中文名称: (S)-3,4-二氨基-4-氧代-丁酸叔丁酯单盐酸盐
• 英文名称: β-tert-butyl-L-aspartic acid amide hydrochloride
• 英文别名: Asp(OtBu)-NH2*HCl；H-Asp(otbu)-NH2hcl；tert-butyl (3S)-3,4-diamino-4-oxobutanoate;hydrochloride
• CAS: 92786-68-0
• 化学式: C₈H₁₆N₂O₃*ClH
• 分子量: 224.688
• InChiKey: MGCQDVMGXZJHTN-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  95.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险类别码：
  R52
• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  (S)-3,4-二氨基-4-氧代-丁酸叔丁酯单盐酸盐 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (S)-3-((S)-2-Amino-4-methylsulfanyl-butyrylamino)-succinamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and biological activity of new peptide segments of gastrin exhibiting gastrin antagonist property

  摘要：

  A series of C-terminal peptide segments of gastrin, i.e., (tert-butyloxycarbonyl)-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxy-carbonyl)-L-tyrosyl-glycyl-L-tryptophyl-L-methionyl-L-asp artic acid amide, and (benzyloxycarbonyl)-L-glutamyl-L-alanyl-L-tyrosyl-glycyl-L-tryptophyl-L -methionyl-L-aspartic acid amide were prepared and were shown to competitively inhibit the binding of labeled human gastrin to its receptors in an isolated gastric mucosal cell preparation and to antagonize the action of gastrin on gastric acid secretion (ED50 from 1.5 to 7 mg/kg) in vivo in the reperfused rat stomach, determined according to the method of Ghosh and Schild. From these studies, it could be concluded that the C-terminal phenylalanine residue, which is of primary importance for intrinsic biological gastrin-like activity, is not essential for binding to gastrin receptors.

  DOI：

  10.1021/jm00378a012

文献信息

• Investigation of peripheral cholecystokinin receptor heterogeneity by cyclic and related linear analogs of CCK26-33. Synthesis and biological properties
  作者：Bruno Charpentier、Christiane Durieux、Isabelle Menant、Bernard P. Roques

  DOI：10.1021/jm00389a002

  日期：1987.6

  by a D-Lys residue in Boc[Nle28,31]CCK27-33, a derivative as active as CCK8. The linear peptide Boc-Asp-Tyr(SO3H)-Nle-D-Lys-Trp-Nle-Asp-Phe-NH2 was cyclized through amide bond formation between the side chains of Asp26 and D-Lys29 to give the peptide Boc-Asp-Tyr(SO3H)-Nle-D-Lys-Trp-Nle-Asp-Phe-NH2. Analogues 1 and 2 were shown to stimulate secretion of amylase from rat pancreas with a potency that

  通过替换柔性Gly29残基，研究了CCK26-33 [Asp-Tyr（SO3H）-Met-Gly-Trp-Met-Asp-Phe-NH2]（CCK8）周围受体的可能异质性在CCK8折叠中，通过Boc [Nle28，31] CCK27-33中的D-Lys残基，具有与CCK8同样活性的衍生物。线性肽Boc-Asp-Tyr（SO3H）-Nle-D-Lys-Trp-Nle-Asp-Phe-NH2通过Asp26和D-Lys29侧链之间的酰胺键形成环化，得到肽Boc-Asp -Tyr（SO3H）-Nle-D-Lys-Trp-Nle-Asp-Phe-NH2。已显示类似物1和2刺激大鼠胰腺淀粉酶的分泌，其效力分别比CCK8低40和80倍。相反，两种肽均作为CCK8诱导的豚鼠回肠收缩的弱拮抗剂（EC50约为10（-5）M）。尽管它们的C末端Asp32残基发生酰胺化，但从1和2中除去苯丙氨酸获得的肽3和4在所