Boc-D-Lys(Boc)-OH p-nitrophenyl ester | 2592-19-0

• 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: Boc-D-Lys(Boc)-OH p-nitrophenyl ester
• 英文别名: N-Boc-N'-Boc-D-lysine-4-nitrophenyl ester；Boc-D-lys (Boc)-ONp；4-Nitrophenyl N2,N6-bis(tert-butoxycarbonyl)-D-lysinate；(4-nitrophenyl) (2R)-2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 2592-19-0
• 化学式: C₂₂H₃₃N₃O₈
• 分子量: 467.519
• InChiKey: LYUXBTAUKJETMS-QGZVFWFLSA-N

物化性质

• 沸点：
  617.0±55.0 °C(Predicted)
• 密度：
  1.183
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -15°C

反应信息

• 作为反应物：
  描述：

  Boc-D-Lys(Boc)-OH p-nitrophenyl ester 在 Cu(II)(2,6-bis(6-monoamino-β-cyclodextrinmethyl)pyridine) 作用下， 以 乙腈 为溶剂， 生成 N2,N6-双-Boc-D-赖氨酸
  参考文献：
  名称：

  配备双（β-环糊精）的非手性铜配合物对氨基酸酯的对映选择性水解

  摘要：

  摘要 研究了两种配备双(β-环糊精) (bisCDs) 的非手性铜 (II) 配合物作为水解酶模型，用于两对具有烷基链的氨基酸酯对映异构体的对映选择性水解。两种 bisCD 配合物以不同的 CD 空腔取向吡啶连接，表示为 CuL 1 ( L 1 = 2,6-bis(6-mono-amino-β-cyclodextrin-methyl)-pyridine) 和 CuL 2 ( L 2 = 2,6-双（3-单氨基-β-环糊精-甲基）-吡啶）。动力学研究表明，与“面对面”bisCD 复合物 CuL 2 相比，“背对背”bisCD 复合物 CuL 1 对所有底物显示出更高的催化效率和更显着的对映选择性。观察到两种复合物的 L-异构体的总体偏好。在 CuL 1 的存在下，通过饱和动力学研究和电喷雾电离质谱（ESI-MS）分析证明了水解过程中催化剂-底物米氏络合物的形成。N-Boc-N'-Boc-赖氨酸

  DOI：

  10.1016/j.molcata.2016.09.009
• 作为产物：
  描述：

  对硝基苯酚 、 二碳酸二叔丁酯 、 D-赖氨酸盐酸盐 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 Boc-D-Lys(Boc)-OH p-nitrophenyl ester
  参考文献：
  名称：

  10.2174/0115701786284263240219080226

  摘要：

  Abstract: Impurities are an integral part of drug substances, even though they have not been studied in the pharmacological evaluation of the Benefit-Risk (BR) profiles. Hence, understanding their origin and controlling them have prime importance during drug substance development. The structures of some of the impurities in lisdexamfetamine dimesylate, a central nervous system stimulant drug, have been confirmed based on literature and analytical data. The study has been undertaken to evaluate impurities arising from oxidative degradation and impurities due to material attributes. All the listed impurities have been identified, synthesized, and characterized by spectral tools. We have, herein, reported the synthesis of two oxidative degradant impurities, 2-hydroxylisdexamfetamine dimesylate and 4-hydroxylisdexafetamine dimesylate. In addition, chiral isomeric impurities of lisdexamfetamine dimesylate as (S,R), (R,S) and (R,R)-lisdexamfetamine dimesylate have also been reported. These impurities have been identified and synthesized, and a control strategy for mitigating risk in lisdexamfetamine dimesylate is provided.

  DOI：

  10.2174/0115701786284263240219080226

文献信息

• Lysine–spermine conjugates: hydrophobic polyamine amides as potent lipopolysaccharide sequestrants
  作者：Mark R. Burns、Stewart J. Wood、Kelly A. Miller、Thuan Nguyen、Jens R. Cromer、Sunil A. David

  DOI：10.1016/j.bmc.2005.01.038

  日期：2005.4

  Lipopolysaccharides (LPS), otherwise termed `endotoxins' are outer-membrane constituents of Gram-negative bacteria. Lipopolysaccharides play a key role in the pathogenesis of `Septic Shock', a major cause of mortality in the critically ill patient. Therapeutic options aimed at limiting downstream systemic inflammatory processes by targeting lipopolysaccharide do not exist at the present time. We have defined the pharmacophore necessary for small molecules to specifically bind and neutralize LPS and, using animal models of sepsis, have shown that the sequestration of circulatory LPS by small molecules is a therapeutically viable strategy. In this paper, the interactions of a focused library of lysine-spermine conjugates with lipopolysaccharide (LPS) have been characterized. Lysine-spermine conjugates with the epsilon-amino terminus of the lysinyl moiety derivatized with long-chain aliphatic hydrophobic substituents in acyl or alkyl linkage bind and neutralize bacterial lipopolysaccharides, and may be of use in the prevention or treatment of endotoxic shock states. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantioselective hydrolysis of amino acid esters by non-chiral copper complexes equipped with bis (β-cyclodextrin)s
  作者：Shan-Shan Xue、Meng Zhao、Jing-Xing Lan、Rui-Rong Ye、Yi Li、Liang-Nian Ji、Zong-Wan Mao

  DOI：10.1016/j.molcata.2016.09.009

  日期：2016.12

  Abstract Two non-chiral copper(II) complexes equipped with bis(β-cyclodextrin)s (bisCDs) were explored as hydrolase models for the enantioselective hydrolysis of two pairs of alkyl chain-possessing amino acid ester enantiomers. The two bisCD complexes are pyridine-linked with different CD cavity orientations, denoted as CuL 1 ( L 1  = 2,6-bis(6-mono-amino-β-cyclodextrin-methyl)-pyridine) and CuL 2

  摘要 研究了两种配备双(β-环糊精) (bisCDs) 的非手性铜 (II) 配合物作为水解酶模型，用于两对具有烷基链的氨基酸酯对映异构体的对映选择性水解。两种 bisCD 配合物以不同的 CD 空腔取向吡啶连接，表示为 CuL 1 ( L 1 = 2,6-bis(6-mono-amino-β-cyclodextrin-methyl)-pyridine) 和 CuL 2 ( L 2 = 2,6-双（3-单氨基-β-环糊精-甲基）-吡啶）。动力学研究表明，与“面对面”bisCD 复合物 CuL 2 相比，“背对背”bisCD 复合物 CuL 1 对所有底物显示出更高的催化效率和更显着的对映选择性。观察到两种复合物的 L-异构体的总体偏好。在 CuL 1 的存在下，通过饱和动力学研究和电喷雾电离质谱（ESI-MS）分析证明了水解过程中催化剂-底物米氏络合物的形成。N-Boc-N'-Boc-赖氨酸