[(S)-5-amino-1-carbamoylpentyl]carbamic acid tert-butyl ester | 58725-24-9

• 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)-5-amino-1-carbamoylpentyl]carbamic acid tert-butyl ester
• 英文别名: (S)-tert-butyl 1,6-diamino-1-oxohexan-2-ylcarbamate；N_α-Boc-L-lysinamide；Boc-Lys-NH2；((S)-5-amino-1-(carbamoyl)pentyl)carbamic acid tert-butyl ester；tBoc-(L)lysine；N^α-Boc-Lys-amid；tert-butyl N-[(2S)-1,6-diamino-1-oxohexan-2-yl]carbamate
• CAS: 58725-24-9
• 化学式: C₁₁H₂₃N₃O₃
• 分子量: 245.322
• InChiKey: JXIXSGAFSRSQAZ-QMMMGPOBSA-N

物化性质

• 沸点：
  437.8±40.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  [(S)-5-amino-1-carbamoylpentyl]carbamic acid tert-butyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis of Peptidoglycan Units with UDP at the Anomeric Position

  摘要：

  一系列UDP-二糖肽化合物被合成为糖基转移酶的合成底物类似物或潜在抑制剂。已经制备了荧光化合物，目的是开发一种筛选方法，用于选择转糖基酶抑制剂。

  DOI：

  10.1135/cccc20051615
• 作为产物：
  描述：

  N6-((苄氧基)羰基)-N2-(叔丁氧基羰基)-L-赖氨酸甲酯 在 palladium on activated charcoal 氨 、 氢气 作用下， 以 甲醇 为溶剂， 生成 [(S)-5-amino-1-carbamoylpentyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Introduction of 5-Formyl-2′-deoxyuridine into a κB Site: Critical Discrimination of a Base Structure in the Major Groove by NFκB p50 Homodimer

  摘要：

  合成了四种寡核苷酸 26-单体，其中包括在δB 位点用 5-甲酰基-2′-脱氧尿苷代替胸苷。其中一种寡核苷酸 26-mers 与 NFκB p50 同源二聚体的结合具有重要的鉴别作用。

  DOI：

  10.1055/s-1999-3084

文献信息

• DIPEPTIDE MIMETICS OF NGF AND BDNF NEUROTROPHINS
  申请人：Seredenin Sergey Borisovich

  公开号：US20110312895A1

  公开（公告）日：2011-12-22

  The invention relates to compounds having either agonist or antagonist activities for the neurotrophins NGF and BDNF and represented by monomeric or dimeric substituted dipeptides that are analogs of the exposed portions of loop 1 or loop 4 regions of these neurotrophins near or at a beta-turn of the respective loop. N-acylated substituents of these dipeptides are biostereoisomers of the amino acid residues preceding these dipeptide sequences in the neurotrophin primary structure. The dimeric structure is produced advantageously by using hexamethylenediamine to which dipeptides are attached via their carboxyl groups. The claimed compounds displayed neuroprotective and differentiation-inducing activities in cellular models and enhanced the amount of phosphorylated tyrosine kinase A and the heat shock proteins Hsp32 and Hsp70 in the concentration range of 10 −9 to 10 −5 M. They also displayed neuroprotective, anti-parkinsonian, anti-stroke, anti-ischemic, anti-depressant and anti-amnestic activities in animal models and were active in experimental models of Alzheimer's disease. These in vivo effects of the claimed compounds are displayed in the dose range of 0.01 to 10 mg/kg when administered intraperitoneally.

  该发明涉及具有神经营养因子NGF和BDNF的激动剂或拮抗剂活性的化合物，这些化合物由单体或二聚体取代二肽代表，这些二肽代表这些神经营养因子的环1或环4区域的暴露部分的类似物，靠近或在各自环的β-转弯处。这些二肽的N-酰化取代物是神经营养因子原始结构中这些二肽序列之前的氨基酸残基的生物立体异构体。通过使用己二胺，优点地产生二聚体结构，二肽通过它们的羧基团连接到己二胺上。所述化合物在细胞模型中显示出神经保护和诱导分化活性，并在浓度范围为10^(-9)到10^(-5)M时增加了磷酸化酪氨酸激酶A和热休克蛋白Hsp32和Hsp70的量。它们还在动物模型中显示出神经保护、抗帕金森病、抗中风、抗缺血、抗抑郁和抗遗忘活性，并在阿尔茨海默病的实验模型中活跃。所述化合物的这些体内效应在腹腔内给药时的剂量范围为0.01至10毫克/千克。
• C-Terminally Pegylated Growth Hormones
  申请人：Zundel Magali

  公开号：US20090105134A1

  公开（公告）日：2009-04-23

  Conjugated growth hormones of the structure (I) are provided together with methods for manufacturing said conjugates. The conjugates are useful in therapy.

  提供具有结构（I）的共轭生长激素以及制造所述共轭物的方法。这些共轭物在治疗中很有用。
• C-Terminal Attachment of Two Chemical Groups to Peptides
  申请人：Peschke Bernd

  公开号：US20100105617A1

  公开（公告）日：2010-04-29

  The present invention relates to a method for C-terminal attachment of two property-modifying groups to a peptide.

  本发明涉及一种将两个性质修饰基团附加到肽的C端的方法。
• Synthesis and reactivity of a bis-sultone cross-linker for peptideconjugation and [¹⁸F]-radiolabelling via unusual “double click” approach
  作者：Thomas Priem、Cédric Bouteiller、David Camporese、Anthony Romieu、Pierre-Yves Renard

  DOI：10.1039/c1ob06600e

  日期：——

  A novel homobifunctional cross-linker based on a bis-sultone benzenic scaffold was synthesised. The potential utility of this bioconjugation reagent was demonstrated through the preparation of an original prosthetic group suitable for the [18F]-labelling of peptides. The labelling strategy is based on the nucleophilic fluorination via the ring-opening of a first sultone moiety followed by the nucleophilic ring-opening of the second remanent sultone by a reactive amine of the biopolymer. Beyond the one-step radiolabelling of the peptide, the second main advantage of this strategy is the release of free sulfonic acid moieties making the separation of the targeted [18F]-tagged sulfonated compound from its non-sulfonated precursor easier and thus faster. This first report of the successful use of a bis-sultone moiety as a versatile bioconjugatable group was demonstrated through a comprehensive reactivity study involving various nucleophiles, especially those commonly found in biopolymers. An illustrative example, highlighting the potential of this unusual and promising “double click” conjugation approach, was devoted to the radiolabelling of a biological relevant peptide.

  我们合成了一种基于双磺酮苯支架的新型同官能团交联剂。通过制备适用于肽[18F]标记的原始修复基团，证明了这种生物连接试剂的潜在用途。这种标记策略的基础是，先通过环状开环作用对第一位素酮分子进行亲核氟化，然后再通过生物聚合物中的活性胺对第二位残余素酮进行亲核环状开环作用。除了一步完成多肽的放射性标记外，这种策略的第二个主要优点是释放出游离的磺酸分子，使目标[18F]标记磺化化合物与其非磺化前体的分离变得更容易、更快捷。通过对各种亲核物，尤其是生物聚合物中常见的亲核物进行全面的反应性研究，首次报道了成功使用双磺酮分子作为多功能生物共轭基团的情况。在对一种生物相关多肽进行放射性标记时，一个实例突出说明了这种不同寻常且前景广阔的 "双击 "共轭方法的潜力。
• Monohaptenic N?-Benzoyl-L-lysine Derivatives as Anaphylactogens: the Importance of the Unsubstituted Carboxyl Group
  作者：Raymond Guenin、Conrad H. Schneider

  DOI：10.1002/hlca.19840670411

  日期：1984.6.20

  Nα-L-Iysine with a 2-carboxy-4, 6-dinitrophenyl (Dncp) haptenic group on the ε-amino function is a potent anaphylactogen in the guinea pig. We prepared Nε -Dncp- Nα-benzoly-L-Iysinamide and Nε-Dncp-Nα-benzoyl-L-lysyl-1-aminopropane where the carboxyl group of Iysine is blocked. Both compounds were non-elections of anaphylaxis.

  Ñ α -L-Iysine与2-羧基4,6二硝基苯基（DNCP）在ε氨基功能半抗原组是在豚鼠的有效的过敏原。我们制备Ñ ε -Dncp- Ñ α -benzoly-L-Iysinamide和Ñ ε -Dncp- Ñ α -苯甲酰基-L-赖氨酰-1-氨基丙烷，其中Iysine的羧基被阻止。两种化合物都不是过敏反应的选择。