Boc-D-Lys(Fmoc)-OH allyl ester | 850863-84-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Boc-D-Lys(Fmoc)-OH allyl ester
• 英文别名: boc-D-lys(Fmoc)-OAllyl；prop-2-enyl (2R)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 850863-84-2
• 化学式: C₂₉H₃₆N₂O₆
• 分子量: 508.615
• InChiKey: HAGYAMXZHNSLNZ-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-D-Lys(Fmoc)-OH allyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 Nε-(9-fluorenylmethoxycarbonyl)-D-lysine allyl ester
  参考文献：
  名称：

  金属光氧化还原催化合成Fmoc-高酪氨酸的便捷途径及其在鱼腥肽环肽全合成中的应用

  摘要：

  在此，我们报告了天然环肽anabaenopeptin F的首次固相全合成，并使用金属光氧化还原催化来克服与制备这些肽中包含的非蛋白氨基酸高酪氨酸相关的关键挑战。从L-高丝氨酸开始，用N -Fmoc-( S )-2-氨基-4-溴丁酸和4-叔丁氧基溴苯伴侣通过金属光氧化还原催化以简单的方式制备对映体纯Fmoc保护的高酪氨酸。将制备的保护氨基酸用于固相肽合成，实现了anabaenopeptin F的全合成，并建立了异亮氨酸残基的立体化学。合成的鱼腥肽 F 的蛋白酶抑制研究表明，在低纳摩尔范围内对羧肽酶 B 具有抑制活性。合成方法的高度收敛性为快速获得N -Fmoc保护的非蛋白和非天然氨基酸以及包含这些氨基酸的复杂生物活性肽的全合成铺平了道路。

  DOI：

  10.1039/d3ob01608k
• 作为产物：
  描述：

  N2-[叔丁氧羰基]-N6-[苄氧羰基]-D-赖氨酸 在 palladium on activated charcoal 氢气 、 碳酸氢钠 、 caesium carbonate 作用下， 反应 3.17h， 生成 Boc-D-Lys(Fmoc)-OH allyl ester
  参考文献：
  名称：

  Solid-Phase Total Synthesis of Oscillamide Y and Analogues

  摘要：

  We report an efficient solid phase synthesis of oscillamide Y and three analogues. The cyclic peptide was prepared using a combination of Fmoc and allyl chemistries and an acid labile Wang type linker. The urea functionality was smoothly incorporated using N-alpha-(4-nitrophenyloxycarbonyl)-N-epsilon-(9-fluorenylmethoxycarbonyl)-D-lysine allyl ester. Coupling to the N-methyl amino acid was readily achieved using HATU, monitoring the reaction using bromophenol blue. Allyl deprotection was accomplished using Pd(PPh3)(4) and dimedone, and cyclization was smoothly accomplished using PyBroP. All reactions were monitored using mass spectrometry methodology. The cyclized materials were cleaved by acidolysis and purified by RP HPLC. In all cases the material isolated was the major product and gave the expected molecular ion information. HPLC comparison with an authentic sample of oscillamide Y showed that the isomer containing L-N-methylalanine and L-homotyrosine was the natural product. H-1 NMR and H-1-H-1 COSY NMR experiments further confirmed this identification. The four compounds were tested as competitive and slow-tight binding inhibitors of chymotrypsin but showed, contrary to literature expectations, no inhibitory activity.

  DOI：

  10.1021/jo970671o

文献信息

• [EN] USE OF CYCLIC ANABAENOPEPTIN-TYPE PEPTIDES FOR THE TREATMENT OF A CONDITION WHEREIN INHIBITION OF CARBOXYPEPTIDASE U IS BENEFICIAL, NOVEL ANABAENOPEPTIN DERIVATIVES AND INTERMEDIATES THEREOF<br/>[FR] UTILISATION DE PEPTIDES CYCLIQUES DE TYPE ANABAENOPEPTINE DESTINES AU TRAITEMENT D'UN ETAT POUR LEQUEL L'INHIBITION DE LA CARBOXYPEPTIDASE U EST BENEFIQUE, DERIVES DE L'ANABAENOPEPTINE ET INTERMEDIAIRES DE CELLE-CI
  申请人：ASTRAZENECA AB

  公开号：WO2005039617A1

  公开（公告）日：2005-05-06

  The use of a compound of formula (I): in a method of manufacturing a medicament for the treatment or prophylaxis of a condition wherein inhibition of carboxypeptidase U is beneficial; specified compounds of formula (I) and compositions comprising a compound of formula (I) and a pharmaceutically acceptable adjuvant, diluent or carrier.

  在制造用于治疗或预防抑制羧肽酶U有益的药物的方法中使用公式（I）的化合物；指定的公式（I）的化合物和包含公式（I）的化合物以及药用可接受的辅料、稀释剂或载体的组合物。
• Homophymamide A, Heterodetic Cyclic Tetrapeptide from a <i>Homophymia</i> sp. Marine Sponge: A Cautionary Note on Configurational Assignment of Peptides That Contain a Ureido Linkage
  作者：Daichi Kanki、Shohei Nakamukai、Yusuke Ogura、Hirosato Takikawa、Yuji Ise、Yasuhiro Morii、Nobuhiro Yamawaki、Tomohiro Takatani、Osamu Arakawa、Shigeru Okada、Shigeki Matsunaga

  DOI：10.1021/acs.jnatprod.1c00336

  日期：2021.6.25

  homophymamide A (1), was isolated from a Homophymia sp. marine sponge. The structure of homophymamide A was determined to be a lower homologue of anabaenopeptins by spectroscopic analysis, chemical degradation, and chemical synthesis. Analysis of the acidic hydrolysate showed that the racemization of Lys took place, leading us to pose a cautionary note on the configurational assignment of peptides that contain

  以前未报道的杂环肽，homophymamide A ( 1 )，是从Homophymia sp. 中分离出来的。海洋海绵。通过光谱分析、化学降解和化学合成，homophymamide A 的结构被确定为 anabaenopeptins 的较低同系物。酸性水解物的分析表明发生了 Lys 的外消旋化，导致我们对包含脲基键的肽的构型分配提出警告。
• Discovery and Synthesis of Namalide Reveals a New Anabaenopeptin Scaffold and Peptidase Inhibitor
  作者：Pradeep Cheruku、Alberto Plaza、Gianluigi Lauro、Jessica Keffer、John R. Lloyd、Giuseppe Bifulco、Carole A. Bewley

  DOI：10.1021/jm201238p

  日期：2012.1.26

  elucidation, and solid-phase synthesis of namalide, a marine natural product, are described. Namalide is a cyclic tetrapeptide; its macrocycle is formed by only three amino acids, with an exocyclic ureido phenylalanine moiety at its C-terminus. The absolute configuration of namalide was established, and analogs were generated through Fmoc-based solid phase peptide synthesis. We found that only natural

  描述了海洋天然产物 namalide 的发现、结构解析和固相合成。Namalide 是一种环状四肽；它的大环仅由三个氨基酸形成，在其 C 端有一个环外脲基苯丙氨酸部分。建立了namalide的绝对构型，并通过基于Fmoc的固相肽合成生成类似物。我们发现只有天然的namalide而不是含有l- Lys或l - allo的类似物-Ile 在亚微摩尔浓度下抑制羧肽酶 A。同时，一种旨在识别 namalide 的蛋白质靶标的反向虚拟筛选方法选择羧肽酶 A 作为第三高得分命中。Namalide 代表了一种新的 anabaenopeptin 型支架，其蛋白酶抑制活性表明 13 元大环内酰胺可以表现出与更常见的六肽相似的活性。
• Use of Cyclic Anabaenopeptin-type Peptides for the Treatment of a Condition Wherein Inhibition of Carboxypeptidase U is Beneficial, Novel Anabaenopeptin Derivatives and Intermediates Thereof
  申请人：Bjorquist Petter

  公开号：US20080039376A1

  公开（公告）日：2008-02-14

  The use of a compound of formula (I): in a method of manufacturing a medicament for the treatment or prophylaxis of a condition wherein inhibition of carboxypeptidase U is beneficial; specified compounds of formula (I) and compositions comprising a compound of formula (I) and a pharmaceutically acceptable adjuvant, diluent or carrier.

  使用式(I)的化合物制造药物的方法，用于治疗或预防抑制羧肽酶U有益的病症；具体化合物为式(I)和包含式(I)化合物和药学上可接受的辅料、稀释剂或载体的组合物。
• Solid-Phase Total Synthesis of Oscillamide Y and Analogues
  作者：Ian R. Marsh、Mark Bradley、Simon J. Teague

  DOI：10.1021/jo970671o

  日期：1997.9.1

  We report an efficient solid phase synthesis of oscillamide Y and three analogues. The cyclic peptide was prepared using a combination of Fmoc and allyl chemistries and an acid labile Wang type linker. The urea functionality was smoothly incorporated using N-alpha-(4-nitrophenyloxycarbonyl)-N-epsilon-(9-fluorenylmethoxycarbonyl)-D-lysine allyl ester. Coupling to the N-methyl amino acid was readily achieved using HATU, monitoring the reaction using bromophenol blue. Allyl deprotection was accomplished using Pd(PPh3)(4) and dimedone, and cyclization was smoothly accomplished using PyBroP. All reactions were monitored using mass spectrometry methodology. The cyclized materials were cleaved by acidolysis and purified by RP HPLC. In all cases the material isolated was the major product and gave the expected molecular ion information. HPLC comparison with an authentic sample of oscillamide Y showed that the isomer containing L-N-methylalanine and L-homotyrosine was the natural product. H-1 NMR and H-1-H-1 COSY NMR experiments further confirmed this identification. The four compounds were tested as competitive and slow-tight binding inhibitors of chymotrypsin but showed, contrary to literature expectations, no inhibitory activity.