Z-L-Ser-L-Tyr-OMe | 24118-03-4

• 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: Z-L-Ser-L-Tyr-OMe
• 英文别名: Z-Ser-Tyr-OMe；N-(N-benzyloxycarbonyl-L-seryl)-L-tyrosine methyl ester；N-(N-Benzyloxycarbonyl-L-seryl)-L-tyrosin-methylester；Benzyloxycarbonyl-seryl-tyrosin-methylester (L)；methyl (2S)-3-(4-hydroxyphenyl)-2-[[(2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 24118-03-4
• 化学式: C₂₁H₂₄N₂O₇
• 分子量: 416.431
• InChiKey: IMQROYWCRPSOCD-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Z-L-Ser-L-Tyr-OMe 在 盐酸 、 亚硝酸特丁酯 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 Z-Ser-Tyr-Gly-Leu-OMe
  参考文献：
  名称：

  Synthesis of a new cyclic analogue of luliberin

  摘要：

  DOI：

  10.1007/bf00630082
• 作为产物：
  描述：

  N-苄氧羰基-L-丝氨酰肼 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 生成 Z-L-Ser-L-Tyr-OMe
  参考文献：
  名称：

  Peptide Derivatives Containing Two Trifunctional Amino Acids

  摘要：

  DOI：

  10.1021/ja01649a019

文献信息

• Understanding nanoindentation unloading curves
  作者：G. M. Pharr、A. Bolshakov

  DOI：10.1557/jmr.2002.0386

  日期：2002.10

  Experiments have shown that nanoindentation unloading curves obtained with Berkovich triangular pyramidal indenters are usually welldescribed by the power-law relation P = α(h − h_f)^m, where h_f is the final depth after complete unloading and α and m are material constants. However, the power-law exponent is not fixed at an integral value, as would be the case for elastic contact by a conical indenter (m = 2) or a flat circular punch (m = 1), but varies from material to material in the range m = 1.2–1.6. A simple model is developed based on observations from finite element simulations of indentation of elastic–plastic materials by a rigid cone that provides a physical explanation for the behavior. The model, which is based on the concept of an indenter with an “effective shape” whose geometry is determined by the shape of the plastic hardness impression formed during indentation, provides a means by which the material constants in the power law relation can be related to more fundamental material properties such as the elastic modulus and hardness. Simple arguments are presented from which the effective indenter shape can be derived from the pressure distribution under the indenter.

  实验表明，使用伯克维奇三角锥形压头获得的纳米压痕卸载曲线通常可以用幂律关系 P = α（h - hf）m 很好地描述，其中 hf 是完全卸载后的最终深度，α 和 m 是材料常数。然而，幂律指数并不像锥形压头（m = 2）或扁圆冲头（m = 1）的弹性接触那样固定为一个整数值，而是在 m = 1.2-1.6 的范围内因材料而异。根据对刚性锥体压入弹塑性材料的有限元模拟观察，建立了一个简单的模型，为这种行为提供了物理解释。该模型基于一个具有 "有效形状 "的压头的概念，其几何形状由压入过程中形成的塑性硬度印痕的形状决定。通过该模型，可以将幂律关系中的材料常数与弹性模量和硬度等更基本的材料特性联系起来。本文提出了一些简单的论点，根据这些论点，可以从压头下的压力分布推导出有效压头形状。
• Scheme for the synthesis of luliberin and analogs
  作者：S. V. Nikolaev、V. F. Martinov

  DOI：10.1007/bf00714941

  日期：——

  Methyl Ester of WillardineB3°-(human insulin) (II). Rf 0.51 (CsHsN--C4HgOH--CH3CO2H--H20, (10:15:3:12)), 0.92 (iso-C3HTOH--25% NH4OH, (7:4:6)), 0.56 (iso-C3HTOH--25% NH4OH--H20, C7:1:2)), 0.95 (CsHsN--CH3COCH3--H20, (1:1:2)) (TLCon SilufolUV-254 plates, spots revealed with the Pauly reagent [5] and from their UV absorption [3]). Electrophoretic mobility: 1.5 (electrophoresis on Whatman No. 1 paper

  WillardineB3°-（人胰岛素）的甲酯（II）。Rf 0.51 (CsHsN--C4HgOH--CH3CO2H--H20, (10:15:3:12)), 0.92 (iso-C3HTOH--25% NH4OH, (7:4:6)), 0.56 (iso-C3HTOH --25% NH4OH--H20, C7:1:2)), 0.95 (CsHsN--CH3COCH3--H20, (1:1:2))（TLCon SilufolUV-254 板，用保利试剂显露斑点 [5 ] 和来自它们的紫外线吸收 [3]）。电泳迁移率：1.5（在Whatman No. 1纸上电泳，pH 1.9，450 V，7 mA，沉积标准：人胰岛素B链的双-S-磺酸盐）。UV 吸收，ima x 267-269 nm，log ~，4.04 (1% CH3CO2H)。氨基酸分析：Asp 3.10 (3)、Thr 1.67 (2)、Ser
• Amino Acids and Peptides. XI. Phosphorus in Organic Synthesis. VI. Application of Diphenyl Phosphorazidate to the Synthesis of Peptides containing Various Functions
  作者：TAKAYUKI SHIOIRI、SHUNICHI YAMADA

  DOI：10.1248/cpb.22.859

  日期：——

  Application of diphenyl phosphorazidate (DPPA) to the synthesis of peptides revealed that the DPPA method is quite general because it can be applied to the formation of peptides containing various functional groups. No difficulties were encountered when the side chains of serine, threonine, valine, glutamine, asparagine, methionine, histidine, tryptophan, and pyroglutamic acid were present in the carboxyl component. Arginine and cysteine showed no trouble when their side chain functions were protected with the nitro and benzyl groups, respectively. Serine, tyrosine, and histidine could be used as the amino component without any protection of the side chains. Fragment coupling of N-benzyloxycarbonylleucylleucine with valylphenylalanine methyl ester hydrochloride by DPPA showed that no racemization occurred.

  将磷酸二苯酯（DPPA）应用于多肽合成的结果表明，DPPA 方法具有很强的通用性，因为它可以用于合成含有各种官能团的多肽。当羧基成分中含有丝氨酸、苏氨酸、缬氨酸、谷氨酰胺、天冬酰胺、蛋氨酸、组氨酸、色氨酸和焦谷氨酸的侧链时，没有遇到任何困难。当精氨酸和半胱氨酸的侧链功能分别受到硝基和苄基的保护时，不会出现问题。丝氨酸、酪氨酸和组氨酸可用作氨基成分，无需对侧链进行任何保护。用 DPPA 将 N-苄氧羰基亮氨酸与戊基苯丙氨酸甲酯盐酸盐进行片段偶联，结果表明没有发生外消旋现象。
• Synthesis and biological activity of peptide antagonists of luliberin (luteinizing hormone-releasing hormone)
  作者：G. W. Moersch、M. C. Rebstock、E. L. Wittle、F. J. Tinney、E. D. Nicolaides、M. P. Hutt、T. F. Mich、J. M. Vandenbelt、R. E. Edgren

  DOI：10.1021/jm00194a010

  日期：1979.8

  analogues of luliberin (luteinizing hormone-releasing hormone) with modifications in the 1 and 6 positions, and in some instances the 10 position, has been prepared. Some of these analogues are potent inhibitors of luliberin in vitro and in vivo. The use of ultraviolet absorption measurements for evaluating peptides containing tyrosine and tryptophan is described. An efficient synthesis of O-methyl-d-tyrosine

  已经制备了一系列在1和6位，并且在某些情况下在10位有修饰的luliberin的des-His2八肽和九肽类似物（促黄体激素释放激素）。这些类似物中的一些是在体外和体内有效的卢立伯林抑制剂。描述了使用紫外线吸收测量来评估包含酪氨酸和色氨酸的肽。报道了O-甲基-d-酪氨酸的有效合成。
• Synthesis of [D-phe3 (NH2); Pro3; D-Ala6]- and [D-Phe2 (NO2); Pro3; D-Ala6]luliberins
  作者：S. V. Burov、O. A. Kaurov、V. F. Martynov、M. P. Smirnova

  DOI：10.1007/bf00571054

  日期：1980.9

  In order to study the influence of substituents of the aromatic ring of D-phenyl-alanine on the inhibiting capacity of luliberian analogs, we have synthesized two new analogs: and luliberin. The synthesis was performed by the fragmentary condensation method using 2+(3+5) and 2+(5+3) schemes. A new and convenient method of obtaining the amide of the C-terminal tetrapeptide of the luliberin sequence

  为了研究D-苯基-丙氨酸的芳环取代基对luliberian类似物抑制能力的影响，我们合成了两个新的类似物：luliberin和luliberin。使用2+(3+5)和2+(5+3)方案通过片段缩合法进行合成。已经开发了一种新的方便的方法来获得羽扇豆素序列的 C 端四肽的酰胺。在片段的缩合中，使用了叠氮化物和添加l-羟基苯并三唑的碳二亚胺合成方法。精氨酸的胍基被硝化保护，而丝氨酸和酪氨酸的羟基不受保护。从十肽中完全消除保护基团是通过在碳上 Pd 上的催化氢化和通过在 0°C 下加入苯甲醚的无水 HF 进行的。受保护的八肽和十肽通过在乙醇中的 Sephadex LH-20 上的凝胶过滤或通过在硅胶板上的制备薄层色谱法进行纯化。最终的肽在 Sephadex CM-25 上通过离子交换层析纯化。