Z-Phe-Ala-NH2 | 50466-66-5

• 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: Z-Phe-Ala-NH2
• 英文别名: (Z)-(S)-Phe-(S)-Ala-OBzl；Z-Phe-Ala-OBzl；benzyl (2S)-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 50466-66-5
• 化学式: C₂₇H₂₈N₂O₅
• 分子量: 460.53
• InChiKey: LVUGIFZELWWKLR-RDPSFJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Phe-Ala-NH2 在 喹啉 、 三(2-氯乙基)胺 、 五氯化磷 作用下， 生成 Z-D-Phe-ψ-L-Ala-OBzl 、 Z-L-Phe-ψ-L-Ala-OBzl
  参考文献：
  名称：

  Conformational mimicry. 3. Synthesis and incorporation of 1,5-disubstituted tetrazole dipeptide analogs into peptides with preservation of chiral integrity: bradykinin

  摘要：

  New synthetic procedures for preparing 1,5-disubstituted tetrazole dipeptide analogues, which are a conformational mimic of the cis amide bond, and incorporating these analogues into longer peptides, such as bradykinin, while maintaining chiral integrity are presented. The simple addition of the organic base, quinoline, to the reaction with PCl5 when generating an imidoyl chloride from the amide was effective in reducing racemization of the N-terminal amino acid residue of the protected tetrazole dipeptide to minimal levels. The resulting tetrazole dipeptide is quite sensitive to base, and the normal procedures of solid-phase synthesis for neutralization were sufficient to cause racemization of the alpha carbon on the C-terminal side of the tetrazole ring. The use of Z for amino protection and benzyl ester for carboxyl protection with differential removal of the Z group by HBr/HOAc has proven a practical route to a wide variety of tetrazole dipeptides. Immediate acylation of the tetrazole dipeptide with a Boc amino acid was necessary to prevent formation of the diketopiperazine, which is favored because of the cis conformation of the amide bond surrogate. Three bradykinin analogues, [L-Pro2-psi[CN4]-L-Ala3]-BK, [L-Ala6-psi[CN4]-L-Ala7]-BK, and [L-Ala6-psi[CN4]-D-Ala7]-BK, in which the peptide bond of a proline residue was replaced with the tetrazole surrogate, were prepared to illustrate the synthetic procedures. The availability of these procedures should increase the use of the tetrazole dipeptide analogue in molecular recognition studies.

  DOI：

  10.1021/jo00027a038
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 吡啶 、 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.17h， 生成 Z-Phe-Ala-NH2
  参考文献：
  名称：

  Amino Acids and Peptides; 67.¹Easy Preparation and Use of Benzyloxycarbonyl Derivatives of Amino Acid Chlorides and α-Hydroxycarboxylic Acid Chlorides

  摘要：

  N-苄氧羰基氨基酸氯化物和α-苄氧羰氧基羧酸氯化物可以通过将相应的羧酸与1-氯-N，N，2-三甲基-1-丙烯-1-胺反应而容易地制备。它们可以直接与O、N和C亲核试剂反应，生成肽、酮和酯。

  DOI：

  10.1055/s-1988-27612

文献信息

• Schelhaas, Michael; Glomsda, Simone; Haensler, Marion, Angewandte Chemie, 1996, vol. 108, # 1, p. 82 - 85
  作者：Schelhaas, Michael、Glomsda, Simone、Haensler, Marion、Jakubke, Hans-Dieter、Waldmann, Herbert

  DOI：——

  日期：——
• Conformational mimicry. 3. Synthesis and incorporation of 1,5-disubstituted tetrazole dipeptide analogs into peptides with preservation of chiral integrity: bradykinin
  作者：Janusz Zabrocki、James B. Dunbar、Keith W. Marshall、Mihaly V. Toth、Garland R. Marshall

  DOI：10.1021/jo00027a038

  日期：1992.1

  New synthetic procedures for preparing 1,5-disubstituted tetrazole dipeptide analogues, which are a conformational mimic of the cis amide bond, and incorporating these analogues into longer peptides, such as bradykinin, while maintaining chiral integrity are presented. The simple addition of the organic base, quinoline, to the reaction with PCl5 when generating an imidoyl chloride from the amide was effective in reducing racemization of the N-terminal amino acid residue of the protected tetrazole dipeptide to minimal levels. The resulting tetrazole dipeptide is quite sensitive to base, and the normal procedures of solid-phase synthesis for neutralization were sufficient to cause racemization of the alpha carbon on the C-terminal side of the tetrazole ring. The use of Z for amino protection and benzyl ester for carboxyl protection with differential removal of the Z group by HBr/HOAc has proven a practical route to a wide variety of tetrazole dipeptides. Immediate acylation of the tetrazole dipeptide with a Boc amino acid was necessary to prevent formation of the diketopiperazine, which is favored because of the cis conformation of the amide bond surrogate. Three bradykinin analogues, [L-Pro2-psi[CN4]-L-Ala3]-BK, [L-Ala6-psi[CN4]-L-Ala7]-BK, and [L-Ala6-psi[CN4]-D-Ala7]-BK, in which the peptide bond of a proline residue was replaced with the tetrazole surrogate, were prepared to illustrate the synthetic procedures. The availability of these procedures should increase the use of the tetrazole dipeptide analogue in molecular recognition studies.
• Amino Acids and Peptides; 67.¹Easy Preparation and Use of Benzyloxycarbonyl Derivatives of Amino Acid Chlorides and α-Hydroxycarboxylic Acid Chlorides
  作者：Ulrich Schmidt、Matthias Kroner、Ulrich Beutler

  DOI：10.1055/s-1988-27612

  日期：——

  N-Benzyloxycarbonyl amino acid chlorides and α-benzyloxycarbonyloxy carboxylic acid chlorides are readily available by treating the corresponding carboxylic acids with 1-chloro-N,N,2-trimethyl-1-propen-1-amine. They can be immediately reacted with O-, N- and C-nucleophiles to afford peptides, ketones and esters.

  N-苄氧羰基氨基酸氯化物和α-苄氧羰氧基羧酸氯化物可以通过将相应的羧酸与1-氯-N，N，2-三甲基-1-丙烯-1-胺反应而容易地制备。它们可以直接与O、N和C亲核试剂反应，生成肽、酮和酯。