methyl L-alanyl-L-isoleucinate | 134356-40-4

• 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: methyl L-alanyl-L-isoleucinate
• 英文别名: L-alanyl-L-isoleucine methyl ester；methyl (2S,3S)-2-[[(2S)-2-aminopropanoyl]amino]-3-methylpentanoate
• CAS: 134356-40-4
• 化学式: C₁₀H₂₀N₂O₃
• 分子量: 216.28
• InChiKey: UEWPOYCHGCGVJS-FXQIFTODSA-N

物化性质

• 沸点：
  337.9±22.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 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：

  methyl L-alanyl-L-isoleucinate 在 吡啶 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 Boc-L-prolyl-L-leucyl-L-alanyl-L-isoleucine-OH
  参考文献：
  名称：

  Toward the Synthesis and Biological Screening of a Cyclotetrapeptide from Marine Bacteria

  摘要：

  首次合成了一种天然存在的四肽环状化合物cyclo-(异亮氨酸-脯氨酸-亮氨酸-丙氨酸)，采用溶液相技术，通过对二肽片段Boc-l-Pro-l-Leu-OH和l-Ala-l-Ile-OMe的偶联实现。去保护线性四肽单元后，其随后的环化反应生成了一种环肽，在各方面均与天然化合物相同。生物活性结果表明，合成的肽对致病性皮肤癣菌和蚯蚓具有抗真菌和抗蠕虫的潜力。

  DOI：

  10.3390/md9010071
• 作为产物：
  描述：

  L-异亮氨酸甲酯盐酸盐 在 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 12.0h， 生成 methyl L-alanyl-L-isoleucinate
  参考文献：
  名称：

  Toward the Synthesis and Biological Screening of a Cyclotetrapeptide from Marine Bacteria

  摘要：

  首次合成了一种天然存在的四肽环状化合物cyclo-(异亮氨酸-脯氨酸-亮氨酸-丙氨酸)，采用溶液相技术，通过对二肽片段Boc-l-Pro-l-Leu-OH和l-Ala-l-Ile-OMe的偶联实现。去保护线性四肽单元后，其随后的环化反应生成了一种环肽，在各方面均与天然化合物相同。生物活性结果表明，合成的肽对致病性皮肤癣菌和蚯蚓具有抗真菌和抗蠕虫的潜力。

  DOI：

  10.3390/md9010071

文献信息

• [EN] MASP INHIBITORY COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS INHIBITEURS DE MASP ET LEURS UTILISATIONS
  申请人：BAYER AG

  公开号：WO2020225095A1

  公开（公告）日：2020-11-12

  The present invention relates to novel Mannose-binding lectin (MBL)-associated serine protease (MASP) inhibitory compounds, as well as analogues and derivatives thereof, to processes for the preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention of diseases and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially for treatment and/or prevention of renal and cardiovascular disorders and of ischemia reperfusion injuries.

  本发明涉及新型甘霖结合凝集素（MBL）相关丝氨酸蛋白酶（MASP）抑制化合物，以及其类似物和衍生物，以及其制备方法，单独或组合用于治疗和/或预防疾病，以及用于生产药物治疗和/或预防疾病，特别是用于治疗和/或预防肾脏和心血管疾病以及缺血再灌注损伤。
• Structures, Sensory Activity, and Dose/Response Functions of 2,5-Diketopiperazines in Roasted Cocoa Nibs (<i>Theobroma cacao</i>)
  作者：Timo Stark、Thomas Hofmann

  DOI：10.1021/jf051313m

  日期：2005.9.1

  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.
• MASP INHIBITORY COMPOUNDS AND USES THEREOF
  申请人：Bayer Aktiengesellschaft

  公开号：US20210246166A1

  公开（公告）日：2021-08-12

  The present invention relates to novel Mannose-binding lectin (MBL)-associated serine protease (MASP) inhibitory compounds, as well as analogues and derivatives thereof, to processes for the preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention of diseases and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially for treatment and/or prevention of renal and cardiovascular disorders and of ischemia reperfusion injuries.
• Toward the Synthesis and Biological Screening of a Cyclotetrapeptide from Marine Bacteria
  作者：Rajiv Dahiya、Hemendra Gautam

  DOI：10.3390/md9010071

  日期：——

  The first synthesis of a naturally occurring tetrapeptide cyclo-(isoleucyl-prolyl-leucyl-alanyl) has been achieved using a solution-phase technique via coupling of dipeptide segments Boc-l-Pro-l-Leu-OH and l-Ala-l-Ile-OMe. Deprotection of the linear tetrapeptide unit and its subsequent cyclization gave a cyclopeptide, identical in all aspects to the naturally occurring compound. Bioactivity results indicated the antifungal and antihelmintic potential of the synthesized peptide against pathogenic dermatophytes and earthworms.

  首次合成了一种天然存在的四肽环状化合物cyclo-(异亮氨酸-脯氨酸-亮氨酸-丙氨酸)，采用溶液相技术，通过对二肽片段Boc-l-Pro-l-Leu-OH和l-Ala-l-Ile-OMe的偶联实现。去保护线性四肽单元后，其随后的环化反应生成了一种环肽，在各方面均与天然化合物相同。生物活性结果表明，合成的肽对致病性皮肤癣菌和蚯蚓具有抗真菌和抗蠕虫的潜力。