Z-Ala-Phe-NH-NH2 | 3235-15-2

• 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-Ala-Phe-NH-NH2
• 英文别名: benzyl N-[(2S)-1-[[(2S)-1-hydrazinyl-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 3235-15-2
• 化学式: C₂₀H₂₄N₄O₄
• 分子量: 384.435
• InChiKey: ZRHNOYQEDZGYNW-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Ala-Phe-NH-NH2 以 吡啶 为溶剂， 反应 5.55h， 生成 N-benzyloxycarbonyl-L-alanyl-L-phenylalanyl-L-proline p-nitrophenyl ester
  参考文献：
  名称：

  Lucente, Gino; Romeo, Aurelio; Cerrini, Silvio, Journal of the Chemical Society. Perkin transactions I, 1980, p. 809 - 816

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-((S)-2-Benzyloxycarbonylamino-propionylamino)-3-phenyl-propionic acid methyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 Z-Ala-Phe-NH-NH2
  参考文献：
  名称：

  Studies on peptides. XLVI. Synthesis of human type corticotropin-like intermediate lobe peptide (CLIP).

  摘要：

  二十二肽，H-Arg-Pro-Val-Lys-Val-Tyr-Pro-Asn-Gly-Ala-Glu-Asp-Glu-Ser-Ala-Gln-Ala-Phe-Pro-Leu-Glu-Phe-OH ，对应于人ACTH（人型促肾上腺皮质激素样中间叶肽，CLIP）的18至39位，通过常规方法和通过在聚合物支持物上的片段缩合程序合成。

  DOI：

  10.1248/cpb.22.1879

文献信息

• Synthèse d'analogues structuraux de l'élédoïsine. 1^repartie: Préparation des produits intermédiaires
  作者：Ed. Sandrin、R. A. Boissonnas

  DOI：10.1002/hlca.19630460518

  日期：——

  The preparation of new dipeptides and tripeptides, which are useful intermediates in the synthesis of Eledoisin analogues, is described.

  描述了新的二肽和三肽的制备，它们是Eledoisin类似物合成中的有用中间体。
• Studies on peptides. XLVI. Synthesis of human type corticotropin-like intermediate lobe peptide (CLIP).
  作者：HIROKI KAWATANI、FUSAKO TAMURA、HARUAKI YAJIMA

  DOI：10.1248/cpb.22.1879

  日期：——

  The docosapeptide, H-Arg-Pro-Val-Lys-Val-Tyr-Pro-Asn-Gly-Ala-Glu-Asp-Glu-Ser-Ala-Gln-Ala-Phe-Pro-Leu-Glu-Phe-OH, corresponding to positions 18 to 39 of human ACTH (human type corticotropin-like intermediate lobe peptide, CLIP) was synthesized by the conventional method and by the fragment condensation procedure on a polymer support.

  二十二肽，H-Arg-Pro-Val-Lys-Val-Tyr-Pro-Asn-Gly-Ala-Glu-Asp-Glu-Ser-Ala-Gln-Ala-Phe-Pro-Leu-Glu-Phe-OH ，对应于人ACTH（人型促肾上腺皮质激素样中间叶肽，CLIP）的18至39位，通过常规方法和通过在聚合物支持物上的片段缩合程序合成。
• Schroeder,E., Justus Liebigs Annalen der Chemie, 1964, vol. 679, p. 207 - 221
  作者：Schroeder,E.

  DOI：——

  日期：——
• Aza-Peptidyl Michael Acceptor and Epoxide Inhibitors—Potent and Selective Inhibitors of Schistosoma mansoni and Ixodes ricinus Legumains (Asparaginyl Endopeptidases)
  作者：Asli Ovat、Fanuel Muindi、Crystal Fagan、Michelle Brouner、Elizabeth Hansell、Jan Dvořák、Daniel Sojka、Petr Kopáček、James H. McKerrow、Conor R. Caffrey、James C. Powers

  DOI：10.1021/jm900849h

  日期：2009.11.26

  Aza-peptide Michael acceptors and epoxides with the general structure of YCO-Ala-Ala-AAsn-trans-CH=CHCOR and YCO-Ala-Ala-AAsn-EP-COR, respectively, are shown to be potent inhibitors of asparaginyl endopeptidases (legumains) from the bloodfluke, Schistosoma mansoni (SmAE), and the hard tick, Ixodes ricinus (IrAE). Structure-activity relationships (SARs) were determined for a set of 41 aza-peptide Michael acceptors and eight aza-peptide epoxides. Both enzymes prefer disubstituted amides to monosubstituted amides in the P1' position, and potency increased as we increased the hydrophobicity of the inhibitor in this position. Extending the inhibitor to P5 resulted in increased potency, especially against IrAE, and both enzymes prefer small over large hydrophobic residues at P2. Aza-peptide Michael acceptor inhibitors are more potent than aza-peptide epoxide inhibitors, and for some of these compounds, second-order inhibiton rate constants are the fastest yet discovered. Given the central functions of these enzymes in both parasites, the data presented here may facilitate the eventual design of selective antiparasitic drugs.
• Lucente, Gino; Romeo, Aurelio; Cerrini, Silvio, Journal of the Chemical Society. Perkin transactions I, 1980, p. 809 - 816
  作者：Lucente, Gino、Romeo, Aurelio、Cerrini, Silvio、Fedeli, Walter、Mazza, Fernando

  DOI：——

  日期：——