Synthesis ( IF 2.2 ) Pub Date : 2018-06-28 , DOI: 10.1055/s-0037-1610202 Marcel Grogg 1 , Donald Hilvert 1 , Albert Beck 1 , Dieter Seebach 1
|
§ This author did all the experiments
Abstract
Novel guanidinium-rich oligopeptide derivatives R-[Adp(X)]8-NH2 are described, which consist of an octa-aspartic acid backbone with argininylated side chains that are derived from the biopolymer cyanophycin [H-(Adp)n-OH]. The Fmoc-Adp(X,Pbf)-OH building blocks for solid-state peptide synthesis (SSPS) of Adp octamers were prepared from Fmoc-Arg(Pbf)-OH and Fmoc-Asp-OAll. Coupling on PAL resin provided four octamers with and without N-terminal fluorescent groups (FAM) and C-terminal amide groups. Milligram quantities of Adp-octamers were isolated after preparative HPLC purification. The structure of the novel guanidinium-rich oligomers is unique insofar as the side chains of the Asp8-backbone include both a guanidino and a carboxylic acid group, the influence of which will be tested with the corresponding ester and amide derivatives that were synthesized in parallel. Unusual cell-penetrating properties of the Adp-octamers are expected.
Novel guanidinium-rich oligopeptide derivatives R-[Adp(X)]8-NH2 are described, which consist of an octa-aspartic acid backbone with argininylated side chains that are derived from the biopolymer cyanophycin [H-(Adp)n-OH]. The Fmoc-Adp(X,Pbf)-OH building blocks for solid-state peptide synthesis (SSPS) of Adp octamers were prepared from Fmoc-Arg(Pbf)-OH and Fmoc-Asp-OAll. Coupling on PAL resin provided four octamers with and without N-terminal fluorescent groups (FAM) and C-terminal amide groups. Milligram quantities of Adp-octamers were isolated after preparative HPLC purification. The structure of the novel guanidinium-rich oligomers is unique insofar as the side chains of the Asp8-backbone include both a guanidino and a carboxylic acid group, the influence of which will be tested with the corresponding ester and amide derivatives that were synthesized in parallel. Unusual cell-penetrating properties of the Adp-octamers are expected.
中文翻译：
蓝藻片段的合成，用于细胞渗透研究
§ 作者做了所有实验
抽象的
描述了新型富胍基寡肽衍生物R- [Adp（X）] 8 -NH 2，其由具有衍生自生物聚合物氰霉素[H-（Adp）n -OH的精氨酰化侧链的八-天冬氨酸主链组成]。由Fmoc-Arg（Pbf）-OH和Fmoc-Asp-OAll制备用于Adp八聚体的固态肽合成（SSPS）的Fmoc-Adp（X，Pbf）-OH构件。在PAL树脂上进行偶联可提供四个带有和不带有N末端荧光基团（FAM）和C末端酰胺基的八聚体。制备型HPLC纯化后，分离出毫克量的Adp-八聚体。就Asp 8的侧链而言，新型富胍基低聚物的结构是独特的-骨架包括胍基和羧酸基团，其影响将用平行合成的相应的酯和酰胺衍生物进行测试。预期Adp八聚体具有异常的细胞穿透特性。
描述了新型富胍基寡肽衍生物R- [Adp（X）] 8 -NH 2，其由具有衍生自生物聚合物氰霉素[H-（Adp）n -OH的精氨酰化侧链的八-天冬氨酸主链组成]。由Fmoc-Arg（Pbf）-OH和Fmoc-Asp-OAll制备用于Adp八聚体的固态肽合成（SSPS）的Fmoc-Adp（X，Pbf）-OH构件。在PAL树脂上进行偶联可提供四个带有和不带有N末端荧光基团（FAM）和C末端酰胺基的八聚体。制备型HPLC纯化后，分离出毫克量的Adp-八聚体。就Asp 8的侧链而言，新型富胍基低聚物的结构是独特的-骨架包括胍基和羧酸基团，其影响将用平行合成的相应的酯和酰胺衍生物进行测试。预期Adp八聚体具有异常的细胞穿透特性。
京公网安备 11010802027423号