Boc-D-Leu-L-Leu-OBn | 150212-97-8

• 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: Boc-D-Leu-L-Leu-OBn
• 英文别名: Boc-D-Leu-L-Leu-Bn；N-(tert-Butoxycarbonyl)-D-leucyl-L-leucine benzyl ester；benzyl (2S)-4-methyl-2-[[(2R)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]pentanoate
• CAS: 150212-97-8
• 化学式: C₂₄H₃₈N₂O₅
• 分子量: 434.576
• InChiKey: FABHBZPIAVSSPZ-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-D-Leu-L-Leu-OBn 在 1% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 2.5h， 以100%的产率得到Boc-D-Leu-L-Leu-OH
  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-亮氨酸 、 L-亮氨酸苄酯盐酸盐(1:1) 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 作用下， 反应 12.0h， 生成 Boc-D-Leu-L-Leu-OBn
  参考文献：
  名称：

  天然产物样环状脂肽的多组分大环化策略：表面活性素和霉菌枯草类似物的合成和抗癌评估。

  摘要：

  描述了针对环状脂肽的多组分大环化策略。该方法依赖于利用Ugi和Passerini多组分反应进行肽和氧代肽的环化，在这里它被用于构建天然产物霉菌枯草杆菌素和表面活性素A的小型类似物文库。该方法是同时掺入一个或两个环外脂质尾部以及大环闭环，这仅是由于大环化步骤的多组分性质而可能实现的。脂肽文库的抗癌活性评估表明，在表面活性素支架中第二脂质部分的安装导致癌细胞中更强的细胞毒性。

  DOI：

  10.1039/c7ob00459a

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。
• Cyclic nonapeptide amides
  申请人：Von Nussbaum Franz

  公开号：US20080070884A1

  公开（公告）日：2008-03-20

  The invention relates to cyclic nonapeptide amides and to methods for their preparation and to their use for the production of medicaments for the treatment and/or prophylaxis of diseases, especially bacterial infectious diseases.

  该发明涉及环状非肽九肽酰胺及其制备方法，以及它们用于生产用于治疗和/或预防疾病，特别是细菌感染性疾病的药物的方法。
• US7718611B2
  申请人：——

  公开号：US7718611B2

  公开（公告）日：2010-05-18