Fmoc-L-Lysine(lauroyl)-OH | 1128181-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-L-Lysine(lauroyl)-OH
• 英文别名: Fmoc-L-Lys(lauroyl)；Fmoc-Lys(lauroyl)-OH；L-Lysine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-N6-(1-oxododecyl)-；(2S)-6-(dodecanoylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid
• CAS: 1128181-21-4
• 化学式: C₃₃H₄₆N₂O₅
• 分子量: 550.739
• InChiKey: UXJNSRCQVANCFJ-PMERELPUSA-N

物化性质

• 熔点：
  126.0-128.0 °C
• 沸点：
  766.6±60.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  40
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  辛酸 、 Fmoc-L-Lysine(lauroyl)-OH 、 、 FMOC-赖氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Lipidated α-Peptide/β-Peptoid Hybrids with Potent Anti-inflammatory Activity

  摘要：

  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.

  DOI：

  10.1021/jm501341h
• 作为产物：
  描述：

  月桂酰氯 、 FMOC-赖氨酸 在 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.25h， 以66%的产率得到Fmoc-L-Lysine(lauroyl)-OH
  参考文献：
  名称：

  Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

  摘要：

  开发了一种新的汇聚合成策略，用于构建多成分自免疫脂肽疫苗。通过新的高效便捷的合成方法制备了四炔基功能葡萄糖衍生物和脂化Fmoc-赖氨酸。将碳水化合物构建块与自免疫脂质基团（三个脂化Fmoc-赖氨酸）在固相支持上偶联。然后，使用铜催化环加成反应将四个A型链球菌B细胞表位（J8）的拷贝连接到糖脂肽上。该方法通过准备第二个疫苗候选者来详细说明，该候选者包含一个额外的杂交T细胞表位。

  DOI：

  10.3762/bjoc.10.181

文献信息

• Structural Requirements for a Lipoamino Acid in Modulating the Anticonvulsant Activities of Systemically Active Galanin Analogues
  作者：Liuyin Zhang、Charles R. Robertson、Brad R. Green、Timothy H. Pruess、H. Steve White、Grzegorz Bulaj

  DOI：10.1021/jm801397w

  日期：2009.3.12

  Introduction of lipoamino acid (LAA), Lys-palmitoyl, and cationization into a series of galanin analogues yielded systemically active anticonvulsant compounds. To study the relationship between the LAA structure and anticonvulsant activity, orthogonally protected LAAs were synthesized in which the Lys side chain was coupled to fatty acids varying in length from C8 to C18 or was coupled to a monodispersed

  将脂氨基酸 (LAA)、Lys-棕榈酰和阳离子化引入一系列甘丙肽类似物，产生具有全身活性的抗惊厥化合物。为了研究 LAA 结构与抗惊厥活性之间的关系，合成了正交保护的 LAA，其中 Lys 侧链与长度从 C 8到 C 18不等的脂肪酸偶联，或与单分散聚乙二醇 PEG 4偶联。全身给药后，测定了甘丙肽受体亲和力、血清稳定性、亲脂性 (log  D ) 和每种新合成类似物在 6 Hz 癫痫小鼠模型中的活性。各种 LAA 或 Lys 的存在（MPEG 4) 不影响修饰肽的受体结合特性，但它们的抗惊厥活性变化很大并且通常与它们的亲脂性相关。我们的结果表明，改变与带正电荷的氨基酸残基相邻的 LAA 残基的长度或极性可以有效地调节甘丙肽类似物的抗癫痫活性。
• 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.
• Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold
  作者：Vincent Fagan、Istvan Toth、Pavla Simerska

  DOI：10.3762/bjoc.10.181

  日期：——

  A novel convergent synthetic strategy for the construction of multicomponent self-adjuvanting lipopeptide vaccines was developed. A tetraalkyne-functionalized glucose derivative and lipidated Fmoc-lysine were prepared by novel efficient and convenient syntheses. The carbohydrate building block was coupled to the self-adjuvanting lipidic moiety (three lipidated Fmoc-lysines) on solid support. Four copies of a group A streptococcal B cell epitope (J8) were then conjugated to the glyco-lipopeptide using a copper-catalyzed cycloaddition reaction. The approach was elaborated by the preparation of a second vaccine candidate which incorporated an additional promiscuous T-helper epitope.

  开发了一种新的汇聚合成策略，用于构建多成分自免疫脂肽疫苗。通过新的高效便捷的合成方法制备了四炔基功能葡萄糖衍生物和脂化Fmoc-赖氨酸。将碳水化合物构建块与自免疫脂质基团（三个脂化Fmoc-赖氨酸）在固相支持上偶联。然后，使用铜催化环加成反应将四个A型链球菌B细胞表位（J8）的拷贝连接到糖脂肽上。该方法通过准备第二个疫苗候选者来详细说明，该候选者包含一个额外的杂交T细胞表位。