H-Tyr-D-Ala-Phe-Glu(<*>)-Val-Val-Lys(<*>)-NH₂ | 143294-03-5

• 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: H-Tyr-D-Ala-Phe-Glu(<*>)-Val-Val-Lys(<*>)-NH₂
• 英文别名: H-Tyr-D-Ala-Phe-Glu(1)-Val-Val-Lys(1)-NH2；(2S,5S,8S,17S)-17-[[(2S)-2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-3-phenylpropanoyl]amino]-3,6,14,18-tetraoxo-2,5-di(propan-2-yl)-1,4,7,13-tetrazacyclooctadecane-8-carboxamide
• CAS: 143294-03-5
• 化学式: C₄₂H₆₁N₉O₉
• 分子量: 836.001
• InChiKey: XYDNLHGWJPRFDR-OJRJOKFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  60
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  293
• 氢给体数：
  10
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Fmoc-Glu(OpNB)-OH 、 Fmoc-L-缬氨酸 、 Fmoc-D-丙氨酸 、 Fmoc-Lys(pNZ)-OH 以14.1%的产率得到H-Tyr-D-Ala-Phe-Glu(<*>)-Val-Val-Lys(<*>)-NH₂
  参考文献：
  名称：

  Semipermanent p-nitrobenzyloxycarbonyl (pNZ) protection of Orn and Lys side chains: prevention of undesired α-Fmoc removal and application to the synthesis of cyclic peptides

  摘要：

  Semipermanent side-chain protection of Orn and Lys with p-nitrobenzyloxycarbonyl (pNZ) for Fmoc/'Bu chemistry does not result in the unwanted removal of alpha-Fmoc that occurs when groups such as Alloc are used for the same application. Furthermore, pNZ can be used in conjuction with p-nitrobenzyl ester (pNB) to prepare cyclic peptides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.043

文献信息

• Conformationally restricted deltorphin analogs
  作者：Peter W. Schiller、Grazyna Weltrowska、Thi M. D. Nguyen、Brian C. Wilkes、Nga N. Chung、Carole Lemieux

  DOI：10.1021/jm00099a025

  日期：1992.10

  of Phe3 in [D-Ala2]deltorphin I with 2-aminoindan-2-carboxylic acid (Aic) or L- or D-2-aminotetralin-2-carboxylic acid (Atc) resulted in agonist compounds which retained the high delta receptor selectivity of the parent peptide. Substitution of a tetrahydroisoquinoline-3-carboxylic acid (Tic) residue in the 2-position of [D-Ala2]deltorphin I and of [Phe4,Nle6]deltorphin produced a partial delta agonist

  通过在肽序列的2或3位上掺入环状苯丙氨酸类似物或通过各种侧链至侧链环化来合成构象受限的deltorphin类似物。在mu，delta和kappa受体选择性结合测定以及豚鼠回肠（GPI）和小鼠输精管（MVD）生物测定中测试了化合物。用2-氨基茚满-2-羧酸（Aic）或L-或D-2-氨基四氢-2-羧酸（Atc）取代[D-Ala2] deltorphin I中的Phe3产生保留高δ受体的激动剂化合物母体肽的选择性。在[D-Ala2] deltorphin I和[Phe4，Nle6] deltorphin的2-位上取代四氢异喹啉-3-羧酸（Tic）残基产生部分δ激动剂，H-Tyr-Tic-Phe-Asp- Val-Val-Gly-NH2，和纯δ拮抗剂，分别为H-Tyr-Tic-Phe-Phe-Leu-Nle-Asp-NH2。后者的拮抗剂表现出高的δ选择性（Ki mu / Kiδ＝ 502），并且在
• Semipermanent p-nitrobenzyloxycarbonyl (pNZ) protection of Orn and Lys side chains: prevention of undesired α-Fmoc removal and application to the synthesis of cyclic peptides
  作者：Albert Isidro-Llobet、Mercedes Álvarez、Fernando Albericio

  DOI：10.1016/j.tetlet.2005.09.043

  日期：2005.11

  Semipermanent side-chain protection of Orn and Lys with p-nitrobenzyloxycarbonyl (pNZ) for Fmoc/'Bu chemistry does not result in the unwanted removal of alpha-Fmoc that occurs when groups such as Alloc are used for the same application. Furthermore, pNZ can be used in conjuction with p-nitrobenzyl ester (pNB) to prepare cyclic peptides. (c) 2005 Elsevier Ltd. All rights reserved.