N2-[叔丁氧羰基]-N6-[芴甲氧羰基]-L-赖氨酸甲酯 | 133628-28-1

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N2-[叔丁氧羰基]-N6-[芴甲氧羰基]-L-赖氨酸甲酯
• 中文别名: N2-[(1,1-二甲基乙氧基)羰基]-N6-[(9H-芴-9-基甲氧基)羰基]-L-赖氨酸甲酯；叔丁氧羰基-N'-芴甲氧羰基-L-赖氨酸-甲酯
• 英文名称: N-α-Boc-N-ε-Fmoc-L-lysine methyl ester
• 英文别名: N-α-tert-Butyloxycarbonyl-N-ε-9-fluorenylmethyloxycarbonyl-L-lysine methyl ester；N_α-(tert-butoxycarbonyl)-N_ε-<(fluoren-9-ylmethoxy)carbonyl>lysine methyl ester；Boc-Lys(Fmoc)-OMe；methyl (2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 133628-28-1
• 化学式: C₂₇H₃₄N₂O₆
• 分子量: 482.577
• InChiKey: NUSZDVABASFMMF-QHCPKHFHSA-N

物化性质

• 沸点：
  653.7±55.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N2-[叔丁氧羰基]-N6-[芴甲氧羰基]-L-赖氨酸甲酯 在 三丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以67%的产率得到NAlpha-BOC-Nε-FMOC-L-赖氨酸
  参考文献：
  名称：

  N-保护的氨基酸和二肽的苯甲酰基，苄基和甲基酯的选择性脱保护以及与双（三丁基锡）氧化物连接的树脂的N-保护的氨基酸苄基酯的脱保护

  摘要：

  各种N -α-Boc，N -α-Cbz或N，N-二甲基氨基保护的氨基酸和二肽的苯甲酸酯，甲基和苄基酯以及与Wang和Pam树脂连接的N -α保护的氨基酸的酯具有在非质子溶剂中用双（三丁基锡）氧化物有效地和化学选择性地裂解该化合物，从而以良好的收率得到相应的羧酸。此外，已经证明在脱保护过程中不存在外消旋作用。该方法的一个限制是不稳定Ñ -Îμ-Fmoc基团的氨基酸酯8和10，Ñ -α-的Fmoc-大号β-丙氨酸连接于王氏树脂23和Cbz基保护基团在Ñ-α-的Boc-N-Iμ-CBZ-大号赖氨酸苄基和甲酯（5和7），分别与Ñ -α-CBZ-大号-alanyl-大号丙氨酸甲酯19的情况下Ñ -在α-保护的二肽中，没有游离氨基酸的迹象表明该肽键不受影响。

  DOI：

  10.1039/p19960000995
• 作为产物：
  描述：

  重氮甲烷 、 NAlpha-BOC-Nε-FMOC-L-赖氨酸 以 乙醚 为溶剂， 反应 0.17h， 以100%的产率得到N2-[叔丁氧羰基]-N6-[芴甲氧羰基]-L-赖氨酸甲酯
  参考文献：
  名称：

  Synthesis of a series of nitrothiophenes with basic or electrophilic substituents and evaluation as radiosensitizers and as bioreductively activated cytotoxins

  摘要：

  A series of 2- and 3-nitrothiophene-5-carboxamides bearing N-(omega-aminoalkyl) side chains has been prepared by treatment of the thiophenecarbonyl chloride with the appropriate (protected) omega-aminoalkylamine. Analogous N-(oxiranylmethyl)nitrothiophene-5-carboxamides have been synthesized by epoxidation of the corresponding N-allylamide. Compounds in both classes were evaluated in vitro both as radiosensitizers of hypoxic mammalian cells and as selective bioreductively activated cytotoxins. The most potent radiosensitizers were those agents with strong tertiary amine bases or oxiranes in the side chain. Studies in vivo showed that 2-methyl-N-[2-(dimethylamino)ethyl]-3-nitrothiophene-5-carboxamide caused slight radiosensitization of the KHT sarcoma in mice given 0.34 mmol kg-1. However, administration of this and related tertiary amines at higher doses was precluded by systemic toxicity.

  DOI：

  10.1021/jm00111a029

文献信息

• Structure–Activity Relationships and Kinetic Studies of Peptidic Antagonists of CBX Chromodomains
  作者：Jacob I. Stuckey、Catherine Simpson、Jacqueline L. Norris-Drouin、Stephanie H. Cholensky、Junghyun Lee、Ryan Pasca、Nancy Cheng、Bradley M. Dickson、Kenneth H. Pearce、Stephen V. Frye、Lindsey I. James

  DOI：10.1021/acs.jmedchem.6b00801

  日期：2016.10.13

  dynamics simulations performed with CBX7 and its endogenous substrate. Herein, we describe the design, synthesis, and structure–activity relationship studies that led to the development of 1 and provide support for our model of CBX7–ligand recognition by examining the binding kinetics of our antagonists with CBX7 as determined by surface-plasmon resonance.

  为了更好地了解甲基赖氨酸（Kme）结合蛋白对各种疾病状态的贡献，我们最近开发并报道了1（UNC3866）的发现，该化学探针靶向Kme结合蛋白的两个家族，即CBX和CDY染色体结构域，具有对CBX4和-7的选择性。1的发现部分通过使用CBX7及其内源底物进行的分子动力学模拟而得以实现。在本文中，我们描述了导致1发展的设计，合成和结构-活性关系研究，并通过检查表面等离子体激元共振所确定的拮抗剂与CBX7的结合动力学，为我们的CBX7-配体识别模型提供了支持。 。
• Recent developments in chemical deprotection of ester functional groups
  作者：Claudio J. Salomon、Ernesto G. Mata、Oreste A. Mascaretti

  DOI：10.1016/s0040-4020(01)90225-x

  日期：1993.4
• Synthesis of a series of nitrothiophenes with basic or electrophilic substituents and evaluation as radiosensitizers and as bioreductively activated cytotoxins
  作者：Michael D. Threadgill、Paul Webb、Peter O'Neill、Matthew A. Naylor、Miriam A. Stephens、Ian J. Stratford、Shirley Cole、Gerald E. Adams、E. Martin Fielden

  DOI：10.1021/jm00111a029

  日期：1991.7

  A series of 2- and 3-nitrothiophene-5-carboxamides bearing N-(omega-aminoalkyl) side chains has been prepared by treatment of the thiophenecarbonyl chloride with the appropriate (protected) omega-aminoalkylamine. Analogous N-(oxiranylmethyl)nitrothiophene-5-carboxamides have been synthesized by epoxidation of the corresponding N-allylamide. Compounds in both classes were evaluated in vitro both as radiosensitizers of hypoxic mammalian cells and as selective bioreductively activated cytotoxins. The most potent radiosensitizers were those agents with strong tertiary amine bases or oxiranes in the side chain. Studies in vivo showed that 2-methyl-N-[2-(dimethylamino)ethyl]-3-nitrothiophene-5-carboxamide caused slight radiosensitization of the KHT sarcoma in mice given 0.34 mmol kg-1. However, administration of this and related tertiary amines at higher doses was precluded by systemic toxicity.
• Selective deprotection of phenacyl, benzyl and methyl esters of N-protected amino acids and dipeptides and N-protected amino acids benzyl ester linked to resins with bis(tributyltin) oxide
  作者：Claudio J. Salomon、Ernesto G. Mata、Oreste A. Mascaretti

  DOI：10.1039/p19960000995

  日期：——

  methyl and benzyl esters of variousN-α-Boc, N-α-Cbz or N,N-dimethylamino protected amino acids and dipeptides, as well as esters of N-α-protected amino acids linked to Wang and Pam resins have been efficiently and chemoselectively cleaved by bis(tributyltin) oxide in aprotic solvents to give the corresponding carboxylic acids in good yields. Moreover, the absence of racemization during the deprotection

  各种N -α-Boc，N -α-Cbz或N，N-二甲基氨基保护的氨基酸和二肽的苯甲酸酯，甲基和苄基酯以及与Wang和Pam树脂连接的N -α保护的氨基酸的酯具有在非质子溶剂中用双（三丁基锡）氧化物有效地和化学选择性地裂解该化合物，从而以良好的收率得到相应的羧酸。此外，已经证明在脱保护过程中不存在外消旋作用。该方法的一个限制是不稳定Ñ -Îμ-Fmoc基团的氨基酸酯8和10，Ñ -α-的Fmoc-大号β-丙氨酸连接于王氏树脂23和Cbz基保护基团在Ñ-α-的Boc-N-Iμ-CBZ-大号赖氨酸苄基和甲酯（5和7），分别与Ñ -α-CBZ-大号-alanyl-大号丙氨酸甲酯19的情况下Ñ -在α-保护的二肽中，没有游离氨基酸的迹象表明该肽键不受影响。