Boc-D-leucine benzyl ester | 158804-50-3

• 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-leucine benzyl ester
• 英文别名: Boc-D-Leu-OBzl；N-Boc-D-leucine benzyl ester；Boc-D-Leu-Bn；benzyl (2R)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 158804-50-3
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: ZSTPUZSOGCNKRO-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-D-leucine benzyl ester 在 N-甲基吗啉 、 盐酸 、 sodium hexamethyldisilazane 、 三乙酰氧基硼氢化钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 溶剂黄146 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 L-lactyl-Pro-ψ(NHCH2)-N-methyl-D-leucine benzyl ester
  参考文献：
  名称：

  Structure–activity relationships of side-chain modified didemnins

  摘要：

  The synthesis and antitumor activity of a novel didemnin B analogue containing a Psi [CH2NH] amide bond surrogate between N-Me-D-Leu(7) and pro(8) are reported. The analogue shows activity (GI(50) = 4 nM) comparable to that of didemnin B (GI(50) = 13 nM) in the NCI-60 tumor cell screen. This result, along with new data from previously reported synthetic didemnin analogues, is discussed within the context of the side-chain SAR for didemnins. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00638-7
• 作为产物：
  描述：

  BOC-D-亮氨酸 、 溴甲苯 在 二环己胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-D-leucine benzyl ester
  参考文献：
  名称：

  Design and Synthesis of Peptides Passing through the Blood-Brain Barrier

  摘要：

  血脑屏障（BBB）是一种高度选择性的膜屏障，调控血液中的物质向脑实质内的转运。目前，从脑部疾病化学治疗的角度出发，如何将生物活性肽或肽类药物递送入脑是一个相当重要的课题。首先合成了名为001-C8的H-MeTyr-Arg-MeArg-d-Leu-NH(CH2)8NH2，以阐明肽穿越BBB所需的结构特异性。在此肽中，Nα-甲基氨基酸和d-氨基酸残基适当地分布，以防止被肽酶降解。此外，还制备了一批001-C8类似物，即多种碱性肽，用于研究肽的结构与其BBB通透性之间的关系。

  DOI：

  10.1246/bcsj.71.699

文献信息

• Design and Synthesis of Peptides Passing through the Blood-Brain Barrier
  作者：Tateaki Wakamiya、Makoto Kamata、Shoichi Kusumoto、Hiroyuki Kobayashi、Yoshimichi Sai、Ikumi Tamai、Akira Tsuji

  DOI：10.1246/bcsj.71.699

  日期：1998.3

  The blood-brain barrier (BBB) is a highly selective membranous barrier regulating the transport of substances in blood into the brain parenchyma. At present, delivery of biologically active peptides or peptide drugs into the brain is quite an important subject from the standpoint of chemotherapy for brain diseases. H–MeTyr–Arg–MeArg–d-Leu–NH(CH2)8NH2 termed 001-C8 was first synthesized to elucidate the structural specificity of peptides for passing through the BBB. The Nα-methylamino acid and d-amino acid residues were appropriately situated in this peptide to protect against the digestion by peptidase. Furthermore, a number of basic peptides were prepared as 001-C8 analogs for studying the relationship between structure and BBB permeability of peptides.

  血脑屏障（BBB）是一种高度选择性的膜屏障，调控血液中的物质向脑实质内的转运。目前，从脑部疾病化学治疗的角度出发，如何将生物活性肽或肽类药物递送入脑是一个相当重要的课题。首先合成了名为001-C8的H-MeTyr-Arg-MeArg-d-Leu-NH(CH2)8NH2，以阐明肽穿越BBB所需的结构特异性。在此肽中，Nα-甲基氨基酸和d-氨基酸残基适当地分布，以防止被肽酶降解。此外，还制备了一批001-C8类似物，即多种碱性肽，用于研究肽的结构与其BBB通透性之间的关系。
• Effect of PNA Backbone Modifications on Cyanine Dye Binding to PNA−DNA Duplexes Investigated by Optical Spectroscopy and Molecular Dynamics Simulations
  作者：Isil Dilek、Marcela Madrid、Rojendra Singh、Christian P. Urrea、Bruce A. Armitage

  DOI：10.1021/ja045145a

  日期：2005.3.1

  used to study the interaction between a cationic cyanine dye and peptide nucleic acid (PNA)-DNA duplexes. This recognition event is important because it leads to a visible color change, signaling successful hybridization of PNA with a complementary DNA strand. We previously proposed that the dye recognized the minor groove of the duplex, using it as a template for the assembly of a helical aggregate

  光谱学和分子动力学模拟已被用于研究阳离子花青染料和肽核酸 (PNA)-DNA 双链体之间的相互作用。这种识别事件很重要，因为它会导致可见的颜色变化，表明 PNA 与互补 DNA 链成功杂交。我们之前提出染料识别双链体的小沟，将其用作组装螺旋聚集体的模板。与此一致，我们现在报告说，当取代基突出到小沟中时，向 PNA 主链添加异丁基会阻碍染料的聚集，但如果被引导出小沟，则效果较弱。紫外-可见光和圆二向色光谱用于比较不同 PNA-DNA 双链体上的聚集，而分子动力学模拟用于确认取代基在不同程度上阻断了小沟，这取决于起始氨基酸的构型。除了取代基的简单空间阻断效应外，模拟表明，将异丁基基团引入小沟会导致沟变窄，双链体变得更加刚性，结构扰动与对骨架修饰的兴趣日益增长有关PNA 在生物和材料科学中的应用。
• From Peptides to Their Alternating Ester-Urea Analogues: Synthesis and Influence of Hydrogen Bonding Motif and Stereochemistry on Aggregation
  作者：Sebastian Hartwig、Jutta Schwarz、Stefan Hecht

  DOI：10.1021/jo902249w

  日期：2010.2.5

  Peptide-mimicking scaffolds with an incorporated ester-urea motif, replacing two adjacent amide residues, were synthesized and their aggregation behavior was studied in dependence of hydrogen bonding sites as well as backbone stereochemistry. Two oligomer series containing either 50% or 100% ester-urea units and either all-(L) or (D)-alt-(L) backbone configuration were prepared via ester and amide couplings, using it divergent/convergent exponential growth strategy. Their aggregation behavior in organic solution was investigated by means of concentration-dependent NMR spectroscopy and compared to the parent peptide series. Interestingly, the naturally occurring peptide scaffold exhibits the largest tendency to associate in combination with the strongest difference in aggregation behavior between all-(L) and (D)-alt-(L) backbone stereochemistry. With increasing incorporation of the ester-urea motif the aggregation strength decreases and become much less dependent on the backbone configuration. The obtained structure-aggregation relationships reveal the importance of the commensurability and multivalency of hydrogen bonding sites as well as conformational restriction for peptide association and should hence aid the design of peptide mimics, such as beta-sheet breakers or gelators.
• Synthetic Studies of Tamandarin B Side Chain Analogues
  作者：Kenneth M. Lassen、Jisun Lee、Madeleine M. Joullié

  DOI：10.1021/jo100457w

  日期：2010.5.7

  The syntheses of three tamandarin B analogues are described. The goal of these studies was to prepare material to determine their relative therapeutic index and to gain an oversight as to their potential for clinical applications.
• Peptide nucleic acids (PNAs) with a functional backbone
  作者：Ask Püschl、Stefano Sforza、Gerald Haaima、Otto Dahl、Peter E. Nielsen

  DOI：10.1016/s0040-4039(98)00862-4

  日期：1998.6

  The synthesis of 10 new T-PNA monomers derived from L-amino acids is presented. The monomers were incorporated into decameric PNA oligomers, and the hybridisation with RNA, DNA and PNA complements studied by thermal stability measurements. (C) 1998 Elsevier Science Ltd. All rights reserved.