Fmoc-Har-OH

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Har-OH
• 英文别名: (2S)-6-(diaminomethylideneazaniumyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoate
• 化学式: C₂₂H₂₆N₄O₄
• 分子量: 410.473
• InChiKey: QRELIJBJYZHTQU-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  、 Fmoc-Har-OH 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以99%的产率得到
  参考文献：
  名称：

  Novel diphenylmethyl-Derived Amide Protecting Group for Efficient Liquid-Phase Peptide Synthesis: AJIPHASE

  摘要：

  An efficient method for the synthesis of peptides bearing an amide at the C-terminal is described. This method involves the attachment of a C-terminal protecting group bearing long aliphatic chains, followed by the repetition of simple reaction and precipitation steps with the combined advantages of liquid-phase peptide synthesis (LPPS) and solid-phase peptide synthesis (SPPS). Using this method, a hydrophobic peptide was successfully synthesized in good yield and high purity, which cannot be obtained satisfactorily by SPPS.

  DOI：

  10.1021/ol302002g

文献信息

• Methods for the production of peptide derivatives
  申请人：Tovi Avi

  公开号：US20060276626A1

  公开（公告）日：2006-12-07

  The invention relates to methods for the preparation of peptides which are a C-terminal amide derivatives by a combination of solid-phase synthesis and post assembly solution phase synthesis. The peptides which are a C-terminal amide derivatives are further converted to peptide acetates. The invention also relates to pure peptide acetates and to protected peptide precursors.

  这项发明涉及一种通过固相合成和后组装溶液相合成相结合的方法制备C-末端酰胺衍生物的肽。这些C-末端酰胺衍生物的肽进一步转化为肽醋酸酯。该发明还涉及纯肽醋酸酯和受保护的肽前体。
• Synthesis and biological evaluation of analogues of the potent ADAM8 inhibitor cyclo(RLsKDK) for the treatment of inflammatory diseases and cancer metastasis
  作者：Victor Yim、Anaïs F.M. Noisier、Kuo-yuan Hung、Jörg W. Bartsch、Uwe Schlomann、Margaret A. Brimble

  DOI：10.1016/j.bmc.2016.06.042

  日期：2016.9

  inflammatory diseases and cancer metastasis. The cyclic peptide cyclo(RLsKDK) has been shown to inhibit the enzymatic activity of ADAM8 with high specificity and potency. Herein we report a structure-activity relationship (SAR) study of cyclo(RLsKDK) that involves the synthesis and biological evaluation of the lead compound and structural analogues thereof. This study provides insight into the ligand-receptor

  金属蛋白酶ADAM8在发炎性疾病和癌症转移的发展中起关键作用。环状肽环（RLsKDK）已显示出以高特异性和高强度抑制ADAM8的酶活性。本文中，我们报道了环（RLsKDK）的结构-活性关系（SAR）研究，该研究涉及铅化合物及其结构类似物的合成和生物学评估。这项研究提供了对控制环（RLsKDK）与ADAM8 Disintegrin域结合的配体-受体相互作用的深刻见解，并为开发炎性疾病和癌症转移的新疗法奠定了基础。
• Biochemical characterization of a cyanobactin arginine-<i>N</i>-prenylase from the autumnalamide biosynthetic pathway
  作者：Claudia Clemente、Nicholas Johnson、Xiaodan Ouyang、Rafael V. Popin、Sergio Dall'Angelo、Matti Wahlsten、Jouni Jokela、Alessandro Colombano、Brunello Nardone、David P. Fewer、Wael E. Houssen

  DOI：10.1039/d2cc01799g

  日期：——

  Biochemical characterization of the prenyltransferase (AutF) from the autumnalamide pathway shows it targets the nitrogen of the guanidinium moiety in arginine and homoarginine.

  秋胺酰胺途径中的异戊二烯基转移酶（AutF）的生化特征表明，它以精氨酸和同工精氨酸的鸟氨基为靶标。
• Lipidated α-Peptide/β-Peptoid Hybrids with Potent Anti-inflammatory Activity
  作者：Sarah L. Skovbakke、Camilla J. Larsen、Peter M. H. Heegaard、Lise Moesby、Henrik Franzyk

  DOI：10.1021/jm501341h

  日期：2015.1.22

  In this study, we investigated, optimized, and characterized a novel subclass of host defense peptide (HDP) mimics based on a-peptide/beta-peptoid hybrid oligomers with an alternating cationic/hydrophobic design with respect to their ability to modulate the pro-inflammatory response by human primary leukocytes upon exposure to bacterial components. Structureactivity studies revealed that certain lipidated a-peptide/beta-peptoid hybrid oligomers possess anti-inflammatory activities in the submicromolar range with low cytotoxicity, and that the anti-inflammatory activity of the HDP mimics is dependent on the length and position of the lipid element(s). The resulting lead compound, Pam-(Lys-beta NSpe)(6)-NH2, blocks LPS-induced cytokine secretion with a potency comparable to that of polymyxin B. The mode of action of this HDP mimic appears not to involve direct LPS interaction since it, in contrast to polymyxin B, displayed only minor activity in the Limulus amebocyte lysate assay. Flow cytometry data showed specific interaction of a fluorophore-labeled lipidated a-peptide/beta-peptoid hybrid with monocytes and granulocytes indicating a cellular target expressed by these leukocyte subsets.
• Solid phase synthesis of trypanothione reductase inhibitors—towards single bead screening
  作者：David Orain、Mark Bradley

  DOI：10.1016/s0040-4039(00)02009-8

  日期：2001.1

  Using solid phase chemistry, inhibitors of trypanothione reductase were synthesised on TentaGel resin using a biologically compatible safety-catch linker. The material released was of high purity, while cleavage kinetics indicated the potential of the system for multiple release. (C) 2001 Elsevier Science Ltd. All rights reserved.