Z-Tyr(OBzl)-Pro-OH | 83280-13-1

• 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-Tyr(OBzl)-Pro-OH
• 英文别名: Z-Tyr(Bzl)-Pro-OH；Z-Tyr(Bzl)-Pro；(2S)-1-[(2S)-2-(phenylmethoxycarbonylamino)-3-(4-phenylmethoxyphenyl)propanoyl]pyrrolidine-2-carboxylic acid
• CAS: 83280-13-1
• 化学式: C₂₉H₃₀N₂O₆
• 分子量: 502.567
• InChiKey: XUGZCSIXRFZNQW-UIOOFZCWSA-N

物化性质

• 熔点：
  68-69 °C
• 沸点：
  762.8±60.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Z-Tyr(OBzl)-Pro-OH 在 palladium on activated charcoal 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、172.37 kPa 条件下， 反应 26.0h， 生成 [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3-N-[3-N'-[tyrosyl-prolylamino]propyl]thymine]-3'-spiro-5''-[4''-amino-1'',2''-oxathiole-2'',2''-dioxide]
  参考文献：
  名称：

  Design and Discovery of a Novel Dipeptidyl-peptidase IV (CD26)-Based Prodrug Approach

  摘要：

  Here we describe a novel type of enzyme-based prodrug approach in which a dipeptide moiety is linked to a nonpeptidic therapeutic drug through an amide bond which is specifically cleaved by the dipeptidyl-peptidase IV ( DPP IV/CD26) enzyme activity present in plasma and on the surface of certain cells. DPP IV has high substrate selectivity for peptides with a proline ( or an alanine) at the penultimate amino acid position at the N-terminus but tolerates a wide range of natural amino acids at the amino terminal end. A variety of dipeptidyl amide prodrugs of anti-HIV TSAO molecules were synthesized and evaluated for their ability to act as substrates for the enzyme. Our data revealed that DPP IV/CD26 can efficiently recognize such prodrugs as substrates, releasing the parent compound. Moreover, it is possible to modify the half-life and the lipophilicity of the prodrugs by changing the nature of the dipeptide. All conjugates have shown marked in vitro antiviral activities irrespective the the nature of the terminal and/or the penultimate amino acid moiety.

  DOI：

  10.1021/jm0606490
• 作为产物：
  描述：

  4-硝基苯基O-苄基-N-[(苄氧基)羰基]-L-酪氨酸酯 、 L-脯氨酸 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到Z-Tyr(OBzl)-Pro-OH
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of acetylsalicylamino acids and peptides

  摘要：

  合成了若干种含水溶性乙酰水杨酰的氨基酸及中性和酸性氨基酸的肽，并对其抗炎活性进行了研究。

  DOI：

  10.1007/s10600-006-0079-5

文献信息

• Elektrochemische Decarboxylierung vonL.-Threonin- und Oligopeptid-Derivaten unter Bildung vonN-Acyl-N, O-acetalen: Herstellung von Oligopeptiden mit Carboxamid-oder Phosphonat-C-Terminus
  作者：Dieter Seebach、Roland Charczuk、Christian Gerber、Philippe Renaud、Heinz Berner、Helmut Schneider

  DOI：10.1002/hlca.19890720302

  日期：1989.5.3

  Electrochemical Decarboxylation of L-Threonine and Oligopeptide Derivatives with Formation of N-Acyl-N, O-acetals: Preparation of Oligopeptides with Amide or Phophonate C-Terminus

  L-苏氨酸和寡肽衍生物的电化学脱羧反应，形成N-酰基-N，O-乙缩醛：酰胺或膦C-末端制备寡肽
• Sobirov, M.M.; Khalikov, Sh.Kh.; Saidov, S.S., Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 7, p. 397 - 405
  作者：Sobirov, M.M.、Khalikov, Sh.Kh.、Saidov, S.S.、Kodirov, M.Z.、Zaitsev, S.V.、et al.

  DOI：——

  日期：——
• Hartrodt; Neubert; Fischer, Pharmazie, 1982, vol. 37, # 3, p. 165 - 169
  作者：Hartrodt、Neubert、Fischer、Schulz、Barth

  DOI：——

  日期：——
• Myelopeptide MP-5 and fluorescent derivatives: Synthesis and biological activity
  作者：L. A. Fonina、A. A. Az’muko、V. N. Kalikhevich、M. L. Lewit、Z. A. Ardemasova、S. A. Gur’yanov、R. G. Belevskaya、M. A. Efremov、E. M. Treshchalina、A. A. Mikhailova

  DOI：10.1134/s106816200804002x

  日期：2008.7

  The Val-Val-Tyr-Pro-Asp bone marrow peptide (MP-5) and its analogue (MP-5-Lys) were synthesized. Fluorescent derivatives, Ftc-MP-5 and MP-5-Lys(Ftc), were prepared. The iological activity of MP-5 and MP-5-Lys was studied in vitro and in vivo. The MP-5 peptide caused 60-84% inhibition of growth of the following mouse cancers: lymphatic leukemia P388, melanoma B-16, and cervical carcinoma CUC-5. These peptides also restored functional activity of T-lymphocytes that was inhibited by metabolic products of the HL-60 leukemic cell line. MP-5-Lys(Ftc) was shown to preserve the functional properties of MP-5 towards T-lymphocytes, but Ftc-MP-5 was practically inactive.
• SEEBACH, DIETER;CHARCZUK, ROLAND;GERBER, CHRISTIAN;RENAUD, PHILIPPE;BERNE+, HELV. CHIM. ACTA, 72,(1989) N, C. 401-425
  作者：SEEBACH, DIETER、CHARCZUK, ROLAND、GERBER, CHRISTIAN、RENAUD, PHILIPPE、BERNE+

  DOI：——

  日期：——