L-alanyl-L-leucine methyl ester

• 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-alanyl-L-leucine methyl ester
• 英文别名: Alanyl-l-leucine methyl ester；methyl (2S)-2-[[(2S)-2-aminopropanoyl]amino]-4-methylpentanoate
• 化学式: C₁₀H₂₀N₂O₃
• 分子量: 216.28
• InChiKey: YXRMSKDLRGNVGS-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-alanyl-L-leucine methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、151.99 kPa 条件下， 反应 6.0h， 生成 Boc-L-Leu-L-Ala-L-Leu-OMe
  参考文献：
  名称：

  Correlation between the Configurational Structure and the Asymmetric Hydrogenation of Δ¹-, Δ²-, and Δ³-Dehydrotripeptides

  摘要：

  对具有β转角结构的Δ1-脱氢三肽（Δ1-DHP）进行了非均相催化氢化，得到相应的三肽，其示踪显示出非常大的消旋过量，与Δ2-和Δ3-DHP得到的产物相比。发现手性诱导的有效差异与各自DHP的构型密切相关。

  DOI：

  10.1246/cl.1989.459
• 作为产物：
  描述：

  N-(苄氧羰基)-L-丙氨酰-L-亮氨酸 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、500.0 kPa 条件下， 反应 24.5h， 生成 L-alanyl-L-leucine methyl ester
  参考文献：
  名称：

  Structures, Sensory Activity, and Dose/Response Functions of 2,5-Diketopiperazines in Roasted Cocoa Nibs (Theobroma cacao)

  摘要：

  The taste compounds inducing the blood-like, metallic bitter taste sensation reported recently for a dichloromethane extract prepared from roasted cocoa nibs were identified as a series of 25 diketopiperazines by means of HPLC degustation, LC-MS/MS, and independent synthesis. Among these 25 compounds, 13 cis-configured diketopiperazines, namely, CYCIO(L-IIe-L-Phe), CYCIO(L-Val-L-Leu), CYCIO(L-Pro-L-Pro), CYCIO(L-IIe-L-Pro), CYCIO(L-Val-L-Tyr), CYCIO(L-Ala-L-Tyr), CYCIO(L-Phe-L-Ser), CYCIO(L-Ala-L-IIe), CYCIO(L-LeU-L-Phe), cyclo(L-Pro-L-Val), CYCIO(L-Pro-L-Thr), CYCIO(L-PrO-L-Tyr), and CYCIO(L-Val-L-Val) were identified for the first time in cocoa. In addition, the taste recognition thresholds for the metallic as well as the bitter taste of the diketopiperazines were determined, and after quantitative analysis by using two diastereomeric diketopiperazines as the internal standards, the sensory impact of the diketopiperazines was evaluated on the basis of their close-over-threshold (DoT) factors calculated as the ratio of the concentration and the threshold concentration of a compound. These data revealed DoT factors above 1.0 exclusively for cis-cyclo(L-Pro-L-Val), cis-cyclo(L-Val-L-Leu), cis-cyclo(L-Ala-L-IIe), cis-cyclo(L-Ala-L-Leu), and cis-cyclo(L-IIe-L-Pro), whereas all of the other diketopiperazines were present below their individual bitter taste threshold concentrations and should therefore not contribute to the cocoa taste. Because the DoT factors do not consider the nonlinear relationship between the concentration and gustatory response of an individual compound, we, for the first time, report on the recording of dose/response functions describing the human bitter taste perception of diketopiperazines more precisely.

  DOI：

  10.1021/jf051313m

文献信息

• Room temperature N-arylation of amino acids and peptides using copper(<scp>i</scp>) and β-diketone
  作者：Krishna K. Sharma、Swagat Sharma、Anurag Kudwal、Rahul Jain

  DOI：10.1039/c5ob00288e

  日期：——

  A mild and efficient method for the N-arylation of zwitterionic amino acids, amino acid esters and peptides is described. The procedure provides the first room temperature synthesis of N-arylated amino acids and peptides using CuI as a catalyst, diketone as a ligand, and aryl iodides as coupling partners. The method is equally applicable for using relatively inexpensive aryl bromides as coupling partners

  描述了一种用于两性离子氨基酸，氨基酸酯和肽的N-芳基化的温和且有效的方法。该方法提供了第一个室温下使用CuI作为催化剂，二酮作为配体，芳基碘化物作为偶联伴侣的N-芳基化氨基酸和多肽的室温合成方法。该方法同样适用于在80°C下使用相对便宜的芳基溴化物作为偶联伙伴。使用该程序，可以有效地以良好至优异的产率偶联含有反应性官能团的电子和空间上不同的芳基卤化物。
• Peptide Macrocyclization Assisted by Traceless Turn Inducers Derived from Ugi Peptide Ligation with Cleavable and Resin-Linked Amines
  作者：Alfredo R. Puentes、Micjel C. Morejón、Daniel G. Rivera、Ludger A. Wessjohann

  DOI：10.1021/acs.orglett.7b01761

  日期：2017.8.4

  multicomponent approach enabling the installation of turn-inducing moieties that facilitate the macrocyclization of short and medium-size oligopeptides is described. The strategy comprises the Ugi ligation of peptide carboxylic acids and isocyanopeptides in the presence of aldehydes and acid or photolabile amines followed by cyclization and cleavage of the backbone N-substituents to render canonical

  描述了一种多组分方法，该方法使得能够安装促进短和中等大小的寡肽的大环化的转角诱导部分。该策略包括在醛和酸或光不稳定胺存在下，肽羧酸和异氰肽的Ugi连接，然后环化和裂解主链N-取代基以提供典型的环肽。使用Rink酰胺树脂在固相上实施该方法导致了一类新的主链酰胺连接基策略。
• Copper(ii) mediated facile and ultra fast peptide synthesis in methanol
  作者：Sachitanand M. Mali、Sandip V. Jadhav、Hosahudya N. Gopi

  DOI：10.1039/c2cc32581k

  日期：——

  A novel, ultrafast, mild and scalable amide bond formation strategy in methanol using simple thioacids and amines is described. The mechanism suggests that the coupling reactions are initially mediated by CuSO4·5H2O and subsequently catalyzed by in situ generated copper sulfide. The pure peptides were isolated in satisfactory yields in less than 5 minutes.

  描述了一种新颖的、超快速的、温和且可扩展的氨基键形成策略，该策略在甲醇中使用简单的硫酸和胺。机制表明，偶联反应最初由硫酸铜·5水合物介导，随后由原位生成的硫化铜催化。纯肽的分离在不到5分钟的时间内获得了令人满意的产率。
• Syntheses and Separations of Diastereomers of Protected-Δ¹-, Δ²-, and Δ³-Dehydrotripeptides
  作者：Chung-gi Shin、Atsushi Kisuno、Yasuchika Yonezawa

  DOI：10.1246/cl.1988.1469

  日期：1988.9.5

  Total eighteen kinds of Δ1-, Δ2-, and Δ3-dehydrotripeptides (DHP) containing of a ΔPhe and two chiral α-amino acid residues were synthesized and the diastereomeric mixture of DHP were subjected to the HPLC separation. From the results and the 1H NMR spectral data, it was found to be significant relationship between the separation and the conformational structure of DHP.

  总共合成了十八种含有ΔPhe和两个手性α-氨基酸残基的Δ1、Δ2和Δ3-脱氨三肽（DHP），并对DHP的顺反异构体混合物进行了HPLC分离。通过结果和1H NMR谱数据的分析，发现DHP的分离与其构象结构之间存在显著关系。
• Synthesis of Chiral 2,4-Chiral 2,4-Dichloro-6-menthoxy-1,3,5-triazines and 2-Chloro-4, 6-Dimenthoxy-1,3,5-triazines as Enantiodifferentiating Coupling Reagents. An X-ray Study on 2,4,6-Trimenthoxy-1,3,5-triazine
  作者：Zbigniew J. Kamiński、Stanislaw W. Markowicz、Beata Kolesińska、Dariusz Martynowski、Marek L. Główka

  DOI：10.1080/00397919808004839

  日期：1998.7

  Abstract Chiral mono-di-and trimenthoxy-1,3,5-triazines ware obtained from natural menthol and cyanuric chloride and applied as enantioselective coupling reagents in the synthesis of dipeptides.

  摘要 以天然薄荷醇和氰尿酰氯为原料制备的手性单二和三薄荷氧基1,3,5-三嗪类化合物，在二肽合成中用作对映选择性偶联剂。