Semipermanent C-Terminal Carboxylic Acid Protecting Group: Application to Solubilizing Peptides and Fragment Condensation

被引：20

作者：

Paradis-Bas, Marta ^{[1
,2
]}

Tulla-Puche, Judit ^{[1
,2
]}

Albericio, Fernando ^{[1
,2
,3
,4
,5
]}

机构：

[1] Inst Res Biomed IRB Barcelona Barcelon, Barcelona 08028, Spain

[2] Networking Ctr Bioengn Biomat & Nanomed, CIBER BBN, Barcelona 08028, Spain

[3] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain

[4] Univ Kwazulu Natal, Sch Chem & Phys, ZA-4001 Durban, South Africa

[5] Yachay Tech, Sch Chem, Yachay City Of Knowledge 100119, Urcuqui, Ecuador

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 02期

关键词：

SOLID-PHASE SYNTHESIS; HYDROPHOBIC PEPTIDES; REDUCTION; AMIDES; BOND; TAG;

D O I：

10.1021/ol5033943

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-methoxy-4-methylsulfinylbenzyl alcohol (Mmsb-OH) safety-catch linker has been described as a useful tool to overcome two obstacles in peptide synthesis: the solubility and fragment condensation of peptides. The incorporation of the linker into an insoluble peptide target, thereby allowing the conjugation of a poly-Lys as a solubilizing tag, notably enhanced the solubility of the peptide. The selective conditions that remove that linker favored its incorporation as a semipermanent C-terminal protecting group, thereby allowing fragment condensation of peptides.

引用

页码：294 / 297

页数：4

共 28 条

[1] Solid-phase synthesis of C-terminal modified peptides [J].