LVFFA | 182912-78-3

• 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: LVFFA
• 英文别名: Leu-Val-Phe-Phe-Ala；(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]propanoic acid
• CAS: 182912-78-3
• 化学式: C₃₂H₄₅N₅O₆
• 分子量: 595.739
• InChiKey: YJIBLBMPEUNXHD-SJSXQSQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  LVFFA 、 (3R,6R,7S,8S,8aS)methyl 6-((3R,6R,7S,8S,8aS)-6-azido-7,8-dihydroxy-5-oxohexahydro-2H-thiazolo[3,2-a]pyridine-3-carboxamido)-7,8-dihydroxy-5-oxohexahydro-2H-thiazolo[3,2-a]pyridine-3-carboxylate 、 2-甲酰基苯硼酸 以 氘代二甲亚砜 为溶剂， 生成
  参考文献：
  名称：

  改进的δ-戊内酰胺模板，可通过硼酸酯形成来组装Aβ-迷你淀粉样物†

  摘要：

  所述6,7,8,8a-顺（清一色顺式的）取代的δ-戊内酰胺10，11和12是用于硼酸酯的形成高亲和力的二醇，优于相应的6,7-反式类似物1，3和4。X射线和NMR结构分析已经确定了六元环构象的差异，这些差异导致了全顺式立体异构体的酯化性能得到改善。同源低聚的顺式δ-戊内酰胺46–48被用作多肽低聚物49–52自组装的多元醇模板。通过动态共价化学。模板具有约5的二醇间隔，适合于由目标肽，2-甲酰基苯基硼酸和相应模板之间的定量反应组装支链肽。根据该策略，四聚体Aβ-最小淀粉样蛋白52由三组分系统中的九个单个分子自发形成。基于三聚体Aβ（32-40）-迷你淀粉样蛋白51的完整顺序分配进行的详细NMR分析确定了其在溶液中的三维结构。

  DOI：

  10.1039/c6ob00565a
• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-丙氨酸 、 Fmoc-L-苯丙氨酸 在 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以15%的产率得到LVFFA
  参考文献：
  名称：

  Design and synthesis of β-strand-fixed peptides inhibiting aggregation of amyloid β-protein

  摘要：

  Aggregation of 42-residue amyloid beta-protein (A beta 42) can be prevented by beta-sheet breaker peptides (BSBps) homologous to LVFFA residues, which are included in a beta-sheet region of A beta 42 aggregates. To enhance the affinity of BSBps to the A beta 42 aggregates, we designed and synthesized beta-strand-fixed peptides (BSFps) whose side chains were cross-linked by ring closing metathesis. Conformation analysis verified that the designed peptides could be fixed in beta-strand conformation. Among the synthesized pentapeptides, 1 and 12, whose side chains of 2nd and 4th residues were cross-linked, significantly inhibited the aggregation of A beta 42. This suggested that beta-strand-fixation of BSBps could enhance their inhibitory activity against the A beta 42 aggregation. However, pentapeptides 1 and 12 had little effect on morphology of A beta 42 aggregates (fibrils) and neurotoxicity of A beta 42 against SH-SY5Y cells.

  DOI：

  10.1016/j.bmc.2020.115676

文献信息

• Design and synthesis of β-strand-fixed peptides inhibiting aggregation of amyloid β-protein
  作者：Fumiya Tanaka、Kana Shibata、Yoko Monobe、Ken-ichi Akagi、Yuichi Masuda

  DOI：10.1016/j.bmc.2020.115676

  日期：2020.9

  Aggregation of 42-residue amyloid beta-protein (A beta 42) can be prevented by beta-sheet breaker peptides (BSBps) homologous to LVFFA residues, which are included in a beta-sheet region of A beta 42 aggregates. To enhance the affinity of BSBps to the A beta 42 aggregates, we designed and synthesized beta-strand-fixed peptides (BSFps) whose side chains were cross-linked by ring closing metathesis. Conformation analysis verified that the designed peptides could be fixed in beta-strand conformation. Among the synthesized pentapeptides, 1 and 12, whose side chains of 2nd and 4th residues were cross-linked, significantly inhibited the aggregation of A beta 42. This suggested that beta-strand-fixation of BSBps could enhance their inhibitory activity against the A beta 42 aggregation. However, pentapeptides 1 and 12 had little effect on morphology of A beta 42 aggregates (fibrils) and neurotoxicity of A beta 42 against SH-SY5Y cells.
• Improved δ-valerolactam templates for the assembly of Aβ-miniamyloids by boronic ester formation
  作者：André Wuttke、Sebastian Nils Fischer、Annika Nebel、Michael Marsch、Armin Geyer

  DOI：10.1039/c6ob00565a

  日期：——

  analogues 1, 3 and 4. X-ray and NMR structure analysis have identified the differences of the six-membered ring conformations which cause the improved esterification properties of the all-cis stereoisomers. The homooligomeric all-cis δ-valerolactams 46–48 are used as polyol templates for the self-assembly of peptidic oligomers 49–52 by dynamic covalent chemistry. The templates have a diol spacing of approximately

  所述6,7,8,8a-顺（清一色顺式的）取代的δ-戊内酰胺10，11和12是用于硼酸酯的形成高亲和力的二醇，优于相应的6,7-反式类似物1，3和4。X射线和NMR结构分析已经确定了六元环构象的差异，这些差异导致了全顺式立体异构体的酯化性能得到改善。同源低聚的顺式δ-戊内酰胺46–48被用作多肽低聚物49–52自组装的多元醇模板。通过动态共价化学。模板具有约5的二醇间隔，适合于由目标肽，2-甲酰基苯基硼酸和相应模板之间的定量反应组装支链肽。根据该策略，四聚体Aβ-最小淀粉样蛋白52由三组分系统中的九个单个分子自发形成。基于三聚体Aβ（32-40）-迷你淀粉样蛋白51的完整顺序分配进行的详细NMR分析确定了其在溶液中的三维结构。