D-Leu-L-Leu-OBn | 1046203-88-6

• 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: D-Leu-L-Leu-OBn
• 英文别名: D-Leu-L-Leu-Bn；benzyl (2S)-2-[[(2R)-2-amino-4-methylpentanoyl]amino]-4-methylpentanoate
• CAS: 1046203-88-6
• 化学式: C₁₉H₃₀N₂O₃
• 分子量: 334.459
• InChiKey: WBNRJPDMGKHHSP-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  Boc-D-Leu-L-Leu-OH 、 D-Leu-L-Leu-OBn 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 作用下， 以 二氯甲烷 为溶剂， 生成 Boc-(D-Leu-L-Leu)2-Bn
  参考文献：
  名称：

  From Peptides to Their Alternating Ester-Urea Analogues: Synthesis and Influence of Hydrogen Bonding Motif and Stereochemistry on Aggregation

  摘要：

  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.

  DOI：

  10.1021/jo902249w
• 作为产物：
  描述：

  Boc-D-Leu-L-Leu-OBn 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到D-Leu-L-Leu-OBn
  参考文献：
  名称：

  MA026的全合成及抗丙型肝炎病毒活性

  摘要：

  介绍了 MA026 的首次全合成及其抗丙型肝炎病毒活性的候选靶蛋白的鉴定。MA026，一种从假单胞菌发酵液中分离的新型脂环肽。RtIB026 由环缩肽、链肽和 N 端 (R)-3-羟基癸酸组成。第一个亚基侧链 2 是通过将脂肪酸部分 4 与三肽 5 偶联来制备的。 L-Leu(10)-D-Gln(11) 处十肽的关键大环化提供了第二个亚基环缩肽 3。两个关键亚基的阶段缩合和最终脱保护得到 MA026。这种收敛的、灵活的、液相合成对于生成 MA026 衍生物用于未来的构效关系研究将是非常宝贵的。传染性丙型肝炎病毒 (HCV) 细胞培养试验表明，MA026 通过以剂量依赖性方式抑制进入过程来抑制 HCV 感染宿主肝细胞。噬菌体展示筛选和表面等离子共振 (SPR) 结合分析确定了 claudin-1，一种 HCV 进入受体，是 MA026 的候选靶蛋白。

  DOI：

  10.1021/ja410145x

文献信息

• Total Synthesis and Anti-Hepatitis C Virus Activity of MA026
  作者：Satomi Shimura、Masahiro Ishima、Syo Nakajima、Toshitaka Fujii、Natsumi Himeno、Kentaro Ikeda、Jesus Izaguirre-Carbonell、Hiroshi Murata、Toshifumi Takeuchi、Shinji Kamisuki、Takahiro Suzuki、Kouji Kuramochi、Koichi Watashi、Susumu Kobayashi、Fumio Sugawara

  DOI：10.1021/ja410145x

  日期：2013.12.18

  The first total synthesis of MA026 and the identification of its candidate target protein for anti-hepatitis C virus activity are presented. MA026, a novel lipocyclodepsipeptide isolated from the fermentation broth of Pseudomonas sp. RtIB026, consists of a cyclodepsipeptide, a chain peptide, and an N-terminal (R)-3-hydroxydecanoic acid. The first subunit, side chain 2, was prepared by coupling fatty

  介绍了 MA026 的首次全合成及其抗丙型肝炎病毒活性的候选靶蛋白的鉴定。MA026，一种从假单胞菌发酵液中分离的新型脂环肽。RtIB026 由环缩肽、链肽和 N 端 (R)-3-羟基癸酸组成。第一个亚基侧链 2 是通过将脂肪酸部分 4 与三肽 5 偶联来制备的。 L-Leu(10)-D-Gln(11) 处十肽的关键大环化提供了第二个亚基环缩肽 3。两个关键亚基的阶段缩合和最终脱保护得到 MA026。这种收敛的、灵活的、液相合成对于生成 MA026 衍生物用于未来的构效关系研究将是非常宝贵的。传染性丙型肝炎病毒 (HCV) 细胞培养试验表明，MA026 通过以剂量依赖性方式抑制进入过程来抑制 HCV 感染宿主肝细胞。噬菌体展示筛选和表面等离子共振 (SPR) 结合分析确定了 claudin-1，一种 HCV 进入受体，是 MA026 的候选靶蛋白。
• 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.