H-Phe-NH2*HBr | 24730-33-4

• 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: H-Phe-NH2*HBr
• 英文别名: L-Phenylalanine-amide hydrobromide；(2S)-2-amino-3-phenylpropanamide;hydrobromide
• CAS: 24730-33-4
• 化学式: BrH*C₉H₁₂N₂O
• 分子量: 245.119
• InChiKey: LZKGPWKKZYKULV-QRPNPIFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.62
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  H-Phe-NH2*HBr 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 L-苯丙氨酰胺
  参考文献：
  名称：

  Zaher, M. R.; El-Sharief, A. M. Sh., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 8, p. 740 - 743

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酰胺 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 H-Phe-NH2*HBr
  参考文献：
  名称：

  Synthesis and effect on gastric secretion of several di-or tripeptides related to proglumide.

  摘要：

  与普洛古米德（PhCO-DL-Glu-NPr2）相关的几种N-酰二肽或三肽被制备，并通过腹腔注射在大鼠身上检查其对胃分泌的影响。PhCOGlu（Phe-NH2）-NPr2、Z-Glu（Phe-NH2）-NPr2、PhCO-Glu（NPr2）-Phe-NH2和PhCO-Asp-(Phe-NH2)-NPr2抑制胃分泌，而PhCO-Glu（Asp-Phe-NH2）-NPr2则刺激胃分泌。在这些肽中，PhCO-Glu（Phe-NH2）-NPr2对胃分泌表现出最强的抑制活性，其效力超过普洛古米德。

  DOI：

  10.1248/cpb.36.3961

文献信息

• Carboxyl-modified amino acids and peptides as protease inhibitors
  作者：Stewart A. Thompson、Peter R. Andrews、Robert P. Hanzlik

  DOI：10.1021/jm00151a018

  日期：1986.1

  mM, and k2 = 0.015 and 0.010 s-1, respectively). Inhibition of DPP-I by 3d provides only the second example of a cysteine protease which is strongly inhibited by a nitrile analogue of a specific substrate. Further studies are needed to determine the generality and potential utility of this finding. Compounds 3e, 3f, and 4e exemplify a new class of specific affinity labels for cysteine proteases whose

  制备几种类型的羧基修饰的氨基酸和肽，它们具有适合于几种代表性蛋白酶之一的N末端修饰（载体片段），并评估了它们对这些酶的抑制作用。羧基修饰（抑制单元）包括（b）CONH 2，（c）CSNH 2，（d）CN，（e）反式-CH ＝ CHCO 2 Me和（f）反式-CH ＝ CHSO 2 Me。载体片段包括NH2（PhCH2）CHX（1），AcNH（PhCH2）CHX（2），H2NCH2CONH（PhCH2）CHX（3）和AcNH（PhCH2）CHCONHCH2X（4）。化合物1b，1d，1e和1f是微粒体和胞质亮氨酸氨基肽酶的竞争性抑制剂（前者的Ki分别为14.8、67、61和3.7 mM，后者分别为14.1、26.4、27.3和8.8 mM） 。化合物1c和亮氨酸硫代酰胺均对这两种酶均无任何可检测的作用。化合物2b-f还是胰凝乳蛋白酶的竞争性抑制剂（Ki分别为13.9、23.0、5.3、30.8和29
• Synthesis and effect on gastric secretion of several di-or tripeptides related to proglumide.
  作者：KOJI IUCHI、MASAHIRO NITTA、KEIZO ITO、KOICHI SHIMOHARA、GORO TSUKAMOT

  DOI：10.1248/cpb.36.3961

  日期：——

  Several N-acyl di-or tripeptides related to proglumide (PhCO-DL-Glu-NPr2) were prepared and their effects on gastric secretion were examined by intraperitoneal injection in rats. PhCOGlu (Phe-NH2)-NPr2, Z-Glu (Phe-NH2)-NPr2, PhCO-Glu (NPr2)-Phe-NH2 and PhCO-Asp-(Phe-NH2)-NPr2 inhibited gastric secretion, while PhCO-Glu (Asp-Phe-NH2)-NPr2 stimulated gastric secretion. Of these peptides, PhCO-Glu (Phe-NH2)-NPr2 showed the most potent inhibitory activity against gastric secretion, and was more potent than proglumide.

  与普洛古米德（PhCO-DL-Glu-NPr2）相关的几种N-酰二肽或三肽被制备，并通过腹腔注射在大鼠身上检查其对胃分泌的影响。PhCOGlu（Phe-NH2）-NPr2、Z-Glu（Phe-NH2）-NPr2、PhCO-Glu（NPr2）-Phe-NH2和PhCO-Asp-(Phe-NH2)-NPr2抑制胃分泌，而PhCO-Glu（Asp-Phe-NH2）-NPr2则刺激胃分泌。在这些肽中，PhCO-Glu（Phe-NH2）-NPr2对胃分泌表现出最强的抑制活性，其效力超过普洛古米德。
• Synthesis of N-acyl-.GAMMA.-D-glutamyl peptide derivatives containing a C-terminal small fragment of cholecystokinin and their effects on gastric secretion.
  作者：KOJI IUCHI、KEIZO ITO、GORO TSUKAMOTO

  DOI：10.1248/cpb.36.3433

  日期：——

  N-Acyl-γ-D-glutamyl peptide derivatives containing a C-terminal small fragment of cholecystokinin were prepared and their effects on gastric secretion were investigated. PhCO-D-Glu(Phe-NH2)-NPr2 and PhCO-D-Glu(Asp-Phe-NH2)-NPr2 inhibited gastric secretion, while PhCO-D-Glu(Met-Asp-Phe-NH2)-NPr2 and PhCO-D-Glu(Trp-Met-Asp-Phe-NH2)-NPr2 stimulated gastric secretion. The substitution of the acyl function at the N-terminal of PhCO-D-Glu(Phe-NH2)-NPr2 affected the activity. Z-D-Glu(Phe-NH2)-NPr2, 4-chlorobenzoyl-D-Glu-(Phe-NH2)-NPr2 and isonicotinoyl-D-Glu(Phe-NH2)-NPr2 were found to have more potent inhibitory activity against gastric secretion than proglumide (PhCO-DL-Glu-NPr2).

  制备了含有胆囊收缩素 C 端小片段的 N-酰基-γ-D-谷氨酰肽衍生物，并研究了它们对胃液分泌的影响。PhCO-D-Glu(Phe-NH2)-NPr2和PhCO-D-Glu(Asp-Phe-NH2)-NPr2抑制胃液分泌，而PhCO-D-Glu(Met-Asp-Phe-NH2)-NPr2和PhCO-D-Glu(Trp-Met-Asp-Phe-NH2)-NPr2刺激胃液分泌。PhCO-D-Glu(Phe-NH2)-NPr2 N 端酰基功能的替代影响了其活性。研究发现，Z-D-Glu(Phe-NH2)-NPr2、4-氯苯甲酰基-D-Glu-(Phe-NH2)-NPr2 和异烟酰基-D-Glu(Phe-NH2)-NPr2 对胃液分泌的抑制活性比丙谷胺（PhCO-DL-Glu-NPr2）更强。
• Effect of piperidine on benzylaspartyl peptides in solution and in the solid phase
  作者：István Schőn、Roberto Colombo、Attila Csehi

  DOI：10.1039/c39830000505

  日期：——

  Basic conditions (e.g. piperidinolysis), used for the removal of the Nα-9-fluorenylmethyloxycarbonyl group, lead to significant cleavage of side-chain benzyl esters of peptides containing benzylaspartyl residues both in solution and solid-phase syntheses; the intermediate imide derivative is slowly transformed to a mixture of piperidides.

  在碱性条件（例如用于去除所述的piperidinolysis），Ñ α -9-芴基，导致含有在溶液中和固相合成苄基天残基的肽的侧链苄基酯类的显著裂解; 中间体酰亚胺衍生物缓慢转化为哌啶的混合物。
• .alpha.-AMINOACYL CONTAINING NEW PEPTIDES WITH GASTRIN EFFECTS AND A
  申请人：Richter Gedeon Vegyeszeti Gyar RT

  公开号：US04172130A1

  公开（公告）日：1979-10-23

  Peptides of the formula: A--Trp--B--Asp--Phe--NH--Y wherein A is tert.-butoxycarbonyl-aminooxy-acyl, benzyloxycarbonyl-aminooxy-acyl, (aminooxy)-acyl, or E-aminooxy-acyl, wherein E is benzoyl or straight-chain or branched C.sub.1-5 aliphatic acyl, B is methionyl, leucyl, norleucyl, norvalyl or 2-amino-decanoyl, and Y is hydrogen or carboxymethoxy, and pharmaceutically acceptable acid-addition salts or complexes thereof have gastric-acid secretion increasing effects.

  公式为：A--Trp--B--Asp--Phe--NH--Y的肽，其中A为tert.-butoxycarbonyl-aminooxy-acyl，benzyloxycarbonyl-aminooxy-acyl，(aminooxy)-acyl或E-aminooxy-acyl，其中E为苯甲酰基或直链或支链C.sub.1-5脂肪族酰基，B为甲硫氨酰基，亮氨酰基，诺亚鲁氨酰基，诺伐氨酰基或2-氨基癸酰基，Y为氢或羧甲氧基，其药学上可接受的酸盐或复合物具有增加胃酸分泌的作用。