(S)-2,6-Diamino-hexanoic acid octyl ester | 16011-73-7

• 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: (S)-2,6-Diamino-hexanoic acid octyl ester
• 英文别名: octyl (2S)-2,6-diaminohexanoate
• CAS: 16011-73-7
• 化学式: C₁₄H₃₀N₂O₂
• 分子量: 258.404
• InChiKey: KIKQWOIUUASIAZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-赖氨酸 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 38.0h， 生成 (S)-2,6-Diamino-hexanoic acid octyl ester
  参考文献：
  名称：

  氨酰-tRNA的微环境和pKa扰动指导阳离子氨基酸的选择

  摘要：

  蛋白质赖氨酸 (Lys) 和精氨酸 (Arg) 在 α-碳和末端带电中心之间具有多个亚甲基。为什么大自然没有选择侧链中亚甲基较少的鸟氨酸 (Orn)、2,4-二氨基丁酸 (Dab) 和 2,3-二氨基丙酸 (Dpr) 仍然是一个重要问题！使用紫外光谱和1 H-NMR 滴定法研究了氨酰-tRNA (aa-tRNA) 模型底物通过分子内内酰胺化自降解的倾向，结果表明 Lys 和 Arg 保持稳定，而 Orn 和 Dab 环化为内酰胺。疏水性辅助表面介导的模型肽形成强调了微环境和 p K a扰动导致区域选择性差（α-胺vs.末端胺）在 Dpr 和其他非蛋白原类似物中。在磷酸盐存在下，α-选择性变得更差，使其不适合肽合成。Lys aa-tRNA 模型底物的优越区域选择性表明，额外的亚甲基桥有助于自然界分离 α-胺和 ε-胺的微环境以合成肽骨架。

  DOI：

  10.1039/d1ob00798j

文献信息

• Lysine esters used as absorption enhancing agents
  申请人：Merck & Co., Inc.

  公开号：EP0162747A1

  公开（公告）日：1985-11-27

  Novel lysine esters used as absorption enhancing agents for gastrointestinally and rectally administered drugs. Also provided are processes for preparation of said lysine ester coupounds as well as pharmaceutical formulations and methods for their use as absorption enhancing agents.

  新型赖氨酸酯可用作胃肠道和直肠给药的促进吸收剂。此外，还提供了上述赖氨酸酯偶联物的制备工艺以及用作吸收促进剂的药物制剂和方法。
• HYALURONIC ACID-BASED AMPHIPHILIC POLYMER, PREPARATION METHOD AND APPLICATION THEREOF
  申请人：BrightGene Bio-Medical Technology Co., Ltd.

  公开号：EP3241852A1

  公开（公告）日：2017-11-08

  Disclosed are a hyaluronic acid-based amphiphilic polymer, preparation method and application thereof. A main chain of the amphiphilic polymer is a hydrophilic hyaluronic acid and can be employed in active targeting, and a side chain thereof is a hydrophobic group represented by Formula (1). The amphiphilic polymer can carry a small molecule anticancer drug. Polymer nanoparticles are obtained via chemical crosslinking, such that the nanoparticles are not readily dissociated outside a cell or in blood, thus ensuring the stability of a drug encapsulated by the nanoparticles. Upon arriving at a tumor tissue, the hyaluronic acid on a surface of the nanoparticle can immediately combine with a CD44 receptor on a surface of a tumor cell, and effectively enter the tumor cell via endocytosis mediated by the receptor, and then quickly de-crosslink to be dissociated. The drug is quickly released, obtaining an enrichment ratio at a tumor site markedly higher than that of the prior art, resulting in a highly effective treatment, and addressing deficiencies such as drug leakage, low carrying efficiency, low occurrence of endocytosis and slow release in a cell.

  本发明公开了一种透明质酸基两亲聚合物、制备方法及其应用。该两亲聚合物的主链是亲水性透明质酸，可用于活性靶向，其侧链是由式（1）表示的疏水基团。两亲性聚合物可携带小分子抗癌药物。聚合物纳米粒子是通过化学交联获得的，因此纳米粒子在细胞外或血液中不易解离，从而确保了纳米粒子包裹药物的稳定性。到达肿瘤组织后，纳米颗粒表面的透明质酸可立即与肿瘤细胞表面的 CD44 受体结合，并通过受体介导的内吞作用有效进入肿瘤细胞，然后迅速去交联解离。药物迅速释放，在肿瘤部位获得的富集率明显高于现有技术，从而获得高效的治疗效果，并解决了药物泄漏、携带效率低、内吞发生率低和在细胞中释放缓慢等不足。
• Hyaluronic acid-based amphiphilic polymer, preparation method and application thereof
  申请人：BrightGene Bio-Medical Technology Co., Ltd.

  公开号：US10292940B2

  公开（公告）日：2019-05-21

  Disclosed are a hyaluronic acid-based amphiphilic polymer, preparation method and application thereof. A main chain of the amphiphilic polymer is a hydrophilic hyaluronic acid and can be employed in active targeting, and a side chain thereof is a hydrophobic group represented by Formula (1). The amphiphilic polymer can carry a small molecule anticancer drug. Polymer nanoparticles are obtained via chemical crosslinking, such that the nanoparticles are not readily dissociated outside a cell or in blood, thus ensuring the stability of a drug encapsulated by the nanoparticles. Upon arriving at a tumor tissue, the hyaluronic acid on a surface of the nanoparticle can immediately combine with a CD44 receptor on a surface of a tumor cell, and effectively enter the tumor cell via endocytosis mediated by the receptor, and then quickly de-crosslink to be dissociated. The drug is quickly released, obtaining an enrichment ratio at a tumor site markedly higher than that of the prior art, resulting in a highly effective treatment, and addressing deficiencies such as drug leakage, low carrying efficiency, low occurrence of endocytosis and slow release in a cell.

  本发明公开了一种透明质酸基两亲聚合物、制备方法及其应用。该两亲聚合物的主链是亲水性透明质酸，可用于活性靶向，其侧链是由式（1）表示的疏水基团。两亲性聚合物可携带小分子抗癌药物。聚合物纳米粒子是通过化学交联获得的，因此纳米粒子在细胞外或血液中不易解离，从而确保了纳米粒子包裹药物的稳定性。到达肿瘤组织后，纳米颗粒表面的透明质酸可立即与肿瘤细胞表面的 CD44 受体结合，并通过受体介导的内吞作用有效进入肿瘤细胞，然后迅速去交联解离。药物迅速释放，在肿瘤部位获得的富集率明显高于现有技术，从而获得高效的治疗效果，并解决了药物泄漏、携带效率低、内吞发生率低和在细胞中释放缓慢等不足。
• METAL-PEPTIDE COMPOSITIONS AND METHODS FOR STIMULATING HAIR GROWTH
  申请人：PROCYTE CORPORATION

  公开号：EP0500745A1

  公开（公告）日：1992-09-02
• Hyaluronic Acid-Based Amphiphilic Polymer, Preparation Method and Application Thereof
  申请人：BrightGene Bio-Medical Technology Co., Ltd.

  公开号：US20180092858A1

  公开（公告）日：2018-04-05

  Disclosed are a hyaluronic acid-based amphiphilic polymer, preparation method and application thereof. A main chain of the amphiphilic polymer is a hydrophilic hyaluronic acid and can be employed in active targeting, and a side chain thereof is a hydrophobic group represented by Formula (1). The amphiphilic polymer can carry a small molecule anticancer drug. Polymer nanoparticles are obtained via chemical crosslinking, such that the nanoparticles are not readily dissociated outside a cell or in blood, thus ensuring the stability of a drug encapsulated by the nanoparticles. Upon arriving at a tumor tissue, the hyaluronic acid on a surface of the nanoparticle can immediately combine with a CD44 receptor on a surface of a tumor cell, and effectively enter the tumor cell via endocytosis mediated by the receptor, and then quickly de-crosslink to be dissociated. The drug is quickly released, obtaining an enrichment ratio at a tumor site markedly higher than that of the prior art, resulting in a highly effective treatment, and addressing deficiencies such as drug leakage, low carrying efficiency, low occurrence of endocytosis and slow release in a cell.