L-leucyl-L-leucyl-L-leucine methyl ester | 76492-19-8

• 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: L-leucyl-L-leucyl-L-leucine methyl ester
• 英文别名: L-Leu-L-Leu-L-Leu-OMe；H-(L-Leu)₃-OMe；H-L-Leu-L-Leu-L-Leu-OMe；L-leucyl=>L-leucyl=>L-leucine methyl ester；L-Leucyl=>L-leucyl=>L-leucin-methylester；(S)-Methyl 2-((S)-2-((S)-2-amino-4-methylpentanamido)-4-methylpentanamido)-4-methylpentanoate；methyl (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoate
• CAS: 76492-19-8
• 化学式: C₁₉H₃₇N₃O₄
• 分子量: 371.52
• InChiKey: DYROXKRDNGGQRL-JYJNAYRXSA-N

物化性质

• 沸点：
  539.0±40.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-leucyl-L-leucyl-L-leucine methyl ester 在 lithium hydroxide monohydrate 、 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.33h， 生成 L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucyl-L-leucine
  参考文献：
  名称：

  Chloride-Assisted Peptide Macrocyclization

  摘要：

  The role of the Cl- anion as a templating agent for the synthesis of cyclopeptides was assessed through the preparation of three new homocyclolysines and other six cyclic peptides by head-to-tail lactamization. Isolated yields of products obtained by chloride-templating approach were considerably higher than those gained by a cation-promoted procedure, whereby, in some cases, only the anion-assisted synthesis yielded the desired cyclopeptides.

  DOI：

  10.1021/acs.orglett.0c00036
• 作为产物：
  描述：

  ((S)-2-氨基-4-甲基戊酰基)-L-亮氨酸甲酯盐酸盐 在 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.33h， 生成 L-leucyl-L-leucyl-L-leucine methyl ester
  参考文献：
  名称：

  Chloride-Assisted Peptide Macrocyclization

  摘要：

  The role of the Cl- anion as a templating agent for the synthesis of cyclopeptides was assessed through the preparation of three new homocyclolysines and other six cyclic peptides by head-to-tail lactamization. Isolated yields of products obtained by chloride-templating approach were considerably higher than those gained by a cation-promoted procedure, whereby, in some cases, only the anion-assisted synthesis yielded the desired cyclopeptides.

  DOI：

  10.1021/acs.orglett.0c00036

文献信息

• Helical foldamer-catalyzed enantioselective 1,4-addition reaction of dialkyl malonates to cyclic enones
  作者：Tomohiro Umeno、Atsushi Ueda、Mitsunobu Doi、Takuma Kato、Makoto Oba、Masakazu Tanaka

  DOI：10.1016/j.tetlet.2019.151301

  日期：2019.12

  -amino acid into L-Leu-based heptapeptides preferentially induced right-handed (P) helical structures. Using 5∼20 mol % of a single helical foldamers-catalyst, enantioselective 1,4-addition reactions of dialkyl malonates to cycloalk-2-enones (5∼7 rings) proceeded to give chiral 3-substituted cycloalkanones with 94∼99% ee in moderate chemical yields, regardless of the ring size of substrates.

  将五元环的α，α-二取代的α-氨基酸引入L-Leu基七肽中，优先诱导右旋（P）螺旋结构。用5〜20mol％的单一螺旋形折叠催化剂，丙二酸二烷基酯与环烷-2-烯酮（5〜7个环）的对映选择性1，4-加成反应进行，得到ee为94〜99％的手性3-取代的环烷酮。不论底物的环大小如何，化学产率均中等。
• 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。
• Mechanism study on the Oligomerization of Amino Acids into Peptides by Phosphorus Trichloride
  作者：Wenjie Zhao、Dongxin Zhao、Kui Lu

  DOI：10.1080/10426500701807467

  日期：2008.1.14

  As treated by phosphorus trichloride, amino acids could oligomerize into polypeptides. Based on the results obtained by 31P-NMR and ESI-MS/MS, a possible reaction mechanism was proposed. The mechanism might undergo a penta-coordinated phosphorus intermediat. The activated amino acid was a five-membered cyclic penta-coordinated phosphorus intermediate. The nucleophilic attack of the amino group from

  经三氯化磷处理后，氨基酸可寡聚化为多肽。基于31P-NMR和ESI-MS/MS的结果，提出了可能的反应机理。该机制可能会经历五配位的磷中间体。活化的氨基酸是五元环状五配位磷中间体。氨基酸或肽的氨基对中间体羰基的亲核攻击导致肽的形成并释放出一当量的二氯化磷酸。反应序列的重复产生了一系列寡肽。
• Engineered transaminopeptidase, aminolysin-S for catalysis of peptide bond formation to give linear and cyclic dipeptides by one-pot reaction
  作者：Hirokazu Usuki、Yoshiko Uesugi、Jiro Arima、Yukihiro Yamamoto、Masaki Iwabuchi、Tadashi Hatanaka

  DOI：10.1039/b914320c

  日期：——

  Aminopeptidase from Streptomyces thermocyaneoviolaceus NBRC14271 was engineered into transaminopeptidase and used to catalyze an aminolysis reaction to give linear and cyclic dipeptides from cost-effective substrates such as the ester derivatives of amino acids.

  将来自热链霉菌NBRC14271的氨肽酶工程化为转氨肽酶，并用于催化氨解反应，以从成本有效的底物（例如氨基酸的酯衍生物）得到线性和环状的二肽。
• 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。