H-L-Lys(Z)-NH2 | 61734-68-7

• 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: H-L-Lys(Z)-NH2
• 英文别名: H-Lys(Cbz)-NH2；Lys(Cbz)-NH2；H-Lys(Z)-NH2；N^ε-benzyloxycarbonyl-L-lysine amide；N^ε-Benzyloxycarbonyl-L-lysin-amid；(S)-2-amino-6-(benzyloxycarbonylamino)hexanamide；benzyl N-[(5S)-5,6-diamino-6-oxohexyl]carbamate
• CAS: 61734-68-7
• 化学式: C₁₄H₂₁N₃O₃
• 分子量: 279.339
• InChiKey: KZEBEQIWVUMFSB-LBPRGKRZSA-N

物化性质

• 沸点：
  527.1±50.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-L-Lys(Z)-NH2 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.58h， 生成 H-Phe-L-Lys(Z)-NH2
  参考文献：
  名称：

  Salvadori; Marastoni; Balboni, Farmaco, Edizione Scientifica, 1987, vol. 42, # 12, p. 931 - 940

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[(2-甲基丙烷-2-基)氧基羰基氨基]-6-(苯基甲氧羰基氨基)己酸 (4-硝基苯基)酯 在 盐酸 、 氨 作用下， 以 甲酸 、 乙腈 为溶剂， 生成 H-L-Lys(Z)-NH2
  参考文献：
  名称：

  [激素-受体相互作用。借助于对碱不稳定的保护基的合成α-促黑素及其信息序列（作者的翻译）]。

  摘要：

  Hormone‐Receptor Interactions. Synthesses of α‐Melanotropin and of Informational Sequences thereof with the Aid of Alcali‐Labile Protecting Groups.The aim of this investigation was to prepare α‐melanotropin and partial sequences thereof for biological investigations in as pure a state as possible. Classical synthesis in solution was chosen as the general approach, because it allows for extensive purification and identification of all intermediates, thus warranting the chemical identity of the products (in contrast to the solidphase methods). The scheme of protection was as follows: for the Nα‐amino groups mostly t‐butoxycarbonyl (BOC‐), sometimes benzyloxycarbonyl (Z‐), for the Nϵ‐amino group of lysine‐(11) 2‐(methylsulfonyl)‐ethoxycarbonyl (MSOC‐), and for the carboxylic acid group of C‐terminal glycine‐(10) 2‐(4‐tolyl‐sulfonyl)‐ethoxy (‐OTSE). This provides for facile and mild selective deprotection of either the α‐amino groups by acidolysis or of the ϵ‐amino group (α‐carboxyl group) by β‐elimination in alcali. A slight molar excess of 0.12N HCl in HCOOH proved to be the method of choice for removing BOC‐; MSOC‐ is stable in acid (even for 30 min in liquid HF) and easily removed in a few minutes by 0.05‐‐0.1N Ba(OH)2; ‐OTSE is removed similarly. Condensation of amino‐acid and peptide derivatives (formation of the peptide link) was performed using active esters (‐ONP; ‐OSU), dicyclohexyl‐carbodiimide (DCCI) with or without 1‐hydroxy‐benzotriazole (HOBT), or carboxylic acid azides wherever histidine was the carboxylic component.More than 50 compounds are described. Those characterized by arabic numerals served to prove that α‐MSH contains two message sequences that are able to trigger melanocyte response: one in the central region ‐His‐Phe‐Arg‐Trp‐, the other in the C‐terminal portion ‐Gly‐Lys‐Pro‐Val · NH2 of the molecule [3].

  DOI：

  10.1002/hlca.19750580724

文献信息

• Modular Imaging Agents Containing Amino Acids and Peptides
  申请人：Schmitthenner Hans F.

  公开号：US20150038672A1

  公开（公告）日：2015-02-05

  Targeting agents are derived from coupling together formed imaging amino acids or formed multi-modal, multi-chelating metal, multi-dye imaging agents, or combinations of these, that may be conjugated directly, or activated, or attached to linkers to which targeting groups, such as peptides, proteins, antibodies, aptamers, or small molecule inhibitors, may be conjugated in the final steps of the synthesis to form a wide variety of TMIAs.

  靶向药物是由耦合在一起的成像氨基酸或成型的多模式、多螯合金属、多染料成像剂所衍生的，或者这些的组合，可以直接共轭，或者被激活，或者附着到连接剂上，连接剂上可以连接靶向基团，如肽、蛋白质、抗体、寡核苷酸或小分子抑制剂，在合成的最后步骤中共轭，形成各种各样的TMIAs。
• Protease-catalysed synthesis of peptides containing histidine and lysine
  作者：Karin Beck-Piotraschke、Hans-Dieter Jakubke

  DOI：10.1016/s0957-4166(98)00134-7

  日期：1998.5

  trypsin-catalysed syntheses of peptides starting from simple acyl donor esters containing histidine at the P1-position (nomenclature according to Schechter and Berger[1]) and lysine derivatives as amino components were examined on the basis of their kinetic parameters. Despite higher specificity constants (kcat/KM) of trypsin-catalysed ester hydrolysis, α-chymotrypsin-catalysed acyl transfer to Nε-unprotected

  在此基础上研究了动力学控制的α-胰凝乳蛋白酶和胰蛋白酶催化的肽的合成，这些肽从在P 1位含有组氨酸的简单酰基供体酯（根据Schechter和Berger [1]的命名法）和赖氨酸衍生物作为氨基成分开始他们的动力学参数。尽管更高的特异性常数（K猫/ K中号）胰蛋白酶催化的酯水解的，α胰凝乳蛋白酶催化的酰基转移到N ε -unprotected赖氨酸衍生物在酰基转移到N得到相比于胰蛋白酶催化的反应更高的肽的产率，而ε胰蛋白酶催化的β-保护的赖氨酸衍生物的收率较高。冷冻系统中α-胰蛋白酶催化的酰基转移反应证明了冷冻的增产作用。使用特定的酯离去基团，可以减少酶的量和反应时间。在冷冻系统中，pH≥9时，H–Lys–OH的ε-氨基充当酰基受体。
• Rigid-rod push–pull naphthalenediimide photosystems
  作者：Naomi Sakai、Adam L. Sisson、Sheshanath Bhosale、Alexandre Fürstenberg、Natalie Banerji、Eric Vauthey、Stefan Matile

  DOI：10.1039/b708449h

  日期：——

  Design, synthesis and evaluation of advanced rigid-rod π-stack photosystems with asymmetric scaffolds are reported. The influence of push–pull rods on self-organization, photoinduced charge separation and photosynthetic activity is investigated and turns out to be surprisingly small overall.

  报告介绍了具有不对称支架的先进刚性杆Ï-叠层光系统的设计、合成和评估。研究了推拉杆对自组织、光诱导电荷分离和光合作用活性的影响，结果表明其总体影响之小令人惊讶。
• Interface Engineering of Synthetic Pores: Towards Hypersensitive Biosensors
  作者：Federico Mora、Duy-Hien Tran、Natalie Oudry、Gerard Hopfgartner、Damien Jeannerat、Naomi Sakai、Stefan Matile

  DOI：10.1002/chem.200701520

  日期：2008.2.18

  accomplished increase in pore activity. The hydrophilic anchors do not interfere with the blockage of the synthetic pore sensors by anionic analytes. In the case of stoichiometric binding of blockers (K(D)=EC(50) of the pore; EC(50)=concentration needed to observe 50 % pore activity), however, the increase in pore activity achieved by hydrophilic anchoring results in improved pore blockage under high dilution

  引入亲水锚固作为一种有前途的策略，以建设性地控制合成孔隙传感器与周围双相环境的各种相互作用。选择人造硬质β桶作为经典的合成多功能孔，并附有无规卷曲的四赖氨酸作为亲水锚。该先进的孔的合成是从市售起始原料开始的32个步骤中完成的。就孔隙活性而言，亲水性锚固的关键影响是从希尔系数n <1到n = 4的变化。该变化证实了成功的抑制竞争性自组装，其中自水相的沉淀是孔隙活性的成功增加的根源。亲水锚不干扰阴离子分析物对合成孔传感器的阻塞。在阻滞剂的化学计量结合中（K（D）=孔隙的EC（50）； EC（50）=观察到50％孔隙活性所需的浓度），通过亲水性锚固实现的孔隙活性增加导致在高稀释条件下改善了孔堵塞。对照确认，这种增加不会发生于不具有化学计量结合的分析物（K（D）> EC（50））。这些结果不仅表明化学计量结合是合成孔传感器灵敏度极限的预期来源，而且还为该问题提供了有希望的解决方案。亲水锚固与靶向孔
• Ordered and Oriented Supramolecular n/p-Heterojunction Surface Architectures: Completion of the Primary Color Collection
  作者：Ravuri S. K. Kishore、Oksana Kel、Natalie Banerji、Daniel Emery、Guillaume Bollot、Jiri Mareda、Alberto Gomez-Casado、Pascal Jonkheijm、Jurriaan Huskens、Plinio Maroni、Michal Borkovec、Eric Vauthey、Naomi Sakai、Stefan Matile

  DOI：10.1021/ja9030648

  日期：2009.8.12

  and molecular modeling data on zipper assembly. Compared to the previously reported blue and red NDIs, yellow NDIs are more pi-acidic, easier to reduce, and harder to oxidize. The optoelectronic matching achieved in yellow POP-NDIs is reflected in quantitative and long-lived photoinduced charge separation, comparable to their red and much better than their blue counterparts. The direct comparison

  在本研究中，我们描述了黄色对低聚苯基萘二亚胺 (POP-NDI) 供体-受体杂化物的合成、表征和拉链组装。此外，我们首次公开了拉链和逐层（LBL）组装以及石英晶体微量天平（QCM）、原子力显微镜（AFM）和拉链分子建模数据的功能比较结果集会。与之前报道的蓝色和红色 NDI 相比，黄色 NDI 更酸，更容易还原，更难氧化。在黄色 POP-NDI 中实现的光电匹配反映在定量和长寿命的光致电荷分离上，可与红色相媲美，但比蓝色好得多。拉链和 LBL 组件的直接比较表明，黄色拉链比蓝色拉链和 LBL 光系统产生更多的光电流。在 QCM 测量中发现的持续线性增长表明，在关键组件厚度处发生光电流饱和是因为更多的电荷在到达电极之前开始重新组合，而不是因为组件中断。所发现的特性，例如显着的临界厚度、强光电流、大填充因子，以及根据 AFM 图像的光滑表面，对于光电性能很重要，并支持高度有序架构的存在。在 QCM

表征谱图