Boc-Leu-Leu-Leu-OMe | 19794-16-2

• 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-Leu-Leu-Leu-OMe
• 英文别名: N-Boc-L-Leu-L-Leu-L-Leu-OMe；Boc-(L-Leu)3-OMe；tert.-Butyloxycarbonyl-Leu-Leu-Leu-methylester；Boc-L-Leu-L-Leu-L-Leu-OMe；methyl (2S)-4-methyl-2-[[(2S)-4-methyl-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]pentanoyl]amino]pentanoate
• CAS: 19794-16-2
• 化学式: C₂₄H₄₅N₃O₆
• 分子量: 471.638
• InChiKey: IUFKKRIHAUGKDR-FHWLQOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Leu-Leu-Leu-OMe 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 L-leucyl-L-leucyl-L-leucine methyl ester
  参考文献：
  名称：

  Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus

  摘要：

  从美国圣地亚哥拉荷亚海岸获得的海洋来源丝状真菌Asteromyces cruciatus 763，产出了新的五肽lajollamide A (1)，以及已知化合物regiolone (2)、hyalodendrin (3)、gliovictin (4)、1N-norgliovicitin (5)和bis-N-norgliovictin (6)。lajollamide A (1)的平面结构通过核磁共振(NMR)光谱和质谱结合确定。lajollamide A (1)的绝对构型通过全合成得到明确解决，合成过程中获得了三个额外的非对映异构体，并揭示了在化学降解过程中l-亮氨酸和l-N-甲基亮氨酸残基发生了意外的酸介导部分消旋化(2:1)。对分离的代谢物的生物活性，特别是抗菌性质进行了系列检测。

  DOI：

  10.3390/md10122912
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-L-leucyl-L-leucine methyl ester 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Boc-Leu-Leu-Leu-OMe
  参考文献：
  名称：

  Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus

  摘要：

  从美国圣地亚哥拉荷亚海岸获得的海洋来源丝状真菌Asteromyces cruciatus 763，产出了新的五肽lajollamide A (1)，以及已知化合物regiolone (2)、hyalodendrin (3)、gliovictin (4)、1N-norgliovicitin (5)和bis-N-norgliovictin (6)。lajollamide A (1)的平面结构通过核磁共振(NMR)光谱和质谱结合确定。lajollamide A (1)的绝对构型通过全合成得到明确解决，合成过程中获得了三个额外的非对映异构体，并揭示了在化学降解过程中l-亮氨酸和l-N-甲基亮氨酸残基发生了意外的酸介导部分消旋化(2:1)。对分离的代谢物的生物活性，特别是抗菌性质进行了系列检测。

  DOI：

  10.3390/md10122912

文献信息

• Dimeric Self‐Assembly of Pyridyl Guanidinium Carboxylates in Polar Solvents
  作者：Muhammad Irfan Ashiq、Biniam F. Tesfatsion、Francesca Gaggini、Sally Dixon、Jeremy D. Kilburn

  DOI：10.1002/chem.201001861

  日期：2010.11.2

  demonstrate the strongest dimerisation in neat DMSO. X‐ray crystal structures of 5 and 6 reveal two different dimerisation architectures in the solid‐state, but both involve carboxylate–guanidinium salt bridges as anticipated, and π–π interactions. Compounds 10–16 incorporating peptidic fragments between the guanidinium and carboxylate groups, showed reduced dimerisation strength with increased amino

  已经制备了一系列吡啶鎓羧酸盐吡啶鎓盐，并且主要使用稀释等温量热法在H 2 O / DMSO混合物中研究了它们的二聚体自组装。化合物5和6在胍基和羧酸酯基团之间的“束缚”区域掺入了芳环，在纯DMSO中表现出最强的二聚作用。5和6的X射线晶体结构揭示了固态中两种不同的二聚结构，但正如预期的那样，它们都涉及羧酸盐-胍盐桥和π-π相互作用。化合物10 – 16在胍基和羧酸酯基团之间掺入肽片段，显示出二聚作用强度降低，氨基酸含量增加，而且在不断增加的含水条件下持续二聚作用，在14和15的情况下高达50％H 2 O / DMSO 。我们在H 2 O / DMSO混合物中的研究程度取决于底物的溶解度10 – 16，而不是自组装的极限。
• Stereoselective reduction of N-hydroxy-α-iminocarbonyl-oligopeptide methyl esters with Zn–MsOH
  作者：Naoki Kise、Shuji Takaoka、Masahiro Yamauchi、Nasuo Ueda

  DOI：10.1016/s0040-4039(02)01752-5

  日期：2002.10

  The reduction of N-hydroxy-α-imino esters with Zn–MsOH in THF afforded α-amino esters in high yields. The reduction of N-hydroxy-α-iminocarbonyl-oligopeptide methyl esters prepared from l-phenylalanine and l-leucine di-, tri-, tetrapeptides gave the corresponding S-formed oligopeptide methyl esters in moderate diastereoselectivities.

  在THF中用Zn-MsOH还原N-羟基-α-亚氨基酯可高产率获得α-氨基酯。由1-苯丙氨酸和1-亮氨酸二-，三-，四肽制备的N-羟基-α-亚氨基羰基-寡肽甲酯的还原得到中等中等非对映选择性的相应的S-形成的寡肽甲酯。
• A New and Efficient Synthesis of Unnatural Amino Acids and Peptides by Selective 3,3-Dimethyldioxirane Side-Chain Oxidation
  作者：Raffaele Saladino、Maurizio Mezzetti、Enrico Mincione、Ines Torrini、Mario Paglialunga Paradisi、Gaia Mastropietro

  DOI：10.1021/jo990185w

  日期：1999.11.1

  N-Boc derivatives of Leu, Met, Thr, Trp, and Pro, the properties of which resemble those of the respective alpha-amino acid residues present in proteins, rapidly oxidize in the presence of 3,3-dimethyldioxirane to give different products depending on the structure of the oxidizable group in the side chain. A high regioselectivity for the oxygen atom insertion into the gamma-CH bond of Leu residues with respect to the weaker alpha-CH bond was observed. A position selectivity in the oxidation of peptides containing more than one Leu residue was also found.
• COMPOUNDS AND METHODS FOR THE LABELLING AND AFFINITY-SELECTION OF PROTEINS
  申请人：Hoffmann Ralf

  公开号：US20110028330A1

  公开（公告）日：2011-02-03

  The present invention relates to kits and methods for the isotopic/isobaric labeling and the subsequent affinity selection and analysis of proteinaceous molecules. In particular, the invention relates to a kit-of-parts comprising a combinatorial plurality of labeling reagent for the labeling of proteinaceous molecules, each labeling reagent comprising an isobaric label component, an isotopic label component, and a reactive group capable of reacting with a proteinaceous molecule, wherein the isotopic label component concomitantly is an affinity tag. The invention is also directed to a corresponding method for the analysis of proteinaceous molecules, comprising labeling at least one subset of the proteinaceous molecules present by employing a kit-of-parts as defined herein and subsequently separating the labeled molecules by affinity purification via the affinity tag comprised in the label. Finally, the invention relates to the uses of such methods for protein expression profiling or proteomic analyses.
• Isolation, Structure Elucidation and Total Synthesis of Lajollamide A from the Marine Fungus Asteromyces cruciatus
  作者：Tobias Gulder、Hanna Hong、Jhonny Correa、Ekaterina Egereva、Jutta Wiese、Johannes Imhoff、Harald Gross

  DOI：10.3390/md10122912

  日期：——

  The marine-derived filamentous fungus Asteromyces cruciatus 763, obtained off the coast of La Jolla, San Diego, USA, yielded the new pentapeptide lajollamide A (1), along with the known compounds regiolone (2), hyalodendrin (3), gliovictin (4), 1N-norgliovicitin (5), and bis-N-norgliovictin (6). The planar structure of lajollamide A (1) was determined by Nuclear Magnetic Resonance (NMR) spectroscopy in combination with mass spectrometry. The absolute configuration of lajollamide A (1) was unambiguously solved by total synthesis which provided three additional diastereomers of 1 and also revealed that an unexpected acid-mediated partial racemization (2:1) of the l-leucine and l-N-Me-leucine residues occurred during the chemical degradation process. The biological activities of the isolated metabolites, in particular their antimicrobial properties, were investigated in a series of assay systems.

  从美国圣地亚哥拉荷亚海岸获得的海洋来源丝状真菌Asteromyces cruciatus 763，产出了新的五肽lajollamide A (1)，以及已知化合物regiolone (2)、hyalodendrin (3)、gliovictin (4)、1N-norgliovicitin (5)和bis-N-norgliovictin (6)。lajollamide A (1)的平面结构通过核磁共振(NMR)光谱和质谱结合确定。lajollamide A (1)的绝对构型通过全合成得到明确解决，合成过程中获得了三个额外的非对映异构体，并揭示了在化学降解过程中l-亮氨酸和l-N-甲基亮氨酸残基发生了意外的酸介导部分消旋化(2:1)。对分离的代谢物的生物活性，特别是抗菌性质进行了系列检测。