scholarly journals Tetrahydropyranyl: A Non-aromatic, Mild-Acid-Labile Group for Hydroxyl Protection in Solid-Phase Peptide Synthesis

ChemistryOpen ◽  
2017 ◽  
Vol 6 (2) ◽  
pp. 206-210 ◽  
Author(s):  
Anamika Sharma ◽  
Iván Ramos-Tomillero ◽  
Ayman El-Faham ◽  
Hortensia Rodríguez ◽  
Beatriz G. de la Torre ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Acid Labile ◽  
Mild Acid ◽  
Labile Group

Synthesis and Solid-Phase Application of a 9-Xanthenyl Handle

2001 ◽  
Vol 56 (6) ◽  
pp. 526-532 ◽  
Author(s):  
Csaba Somlai ◽  
Péter Hegyes ◽  
Róbert Fenyö ◽  
Gábor K. Tóth ◽  
Botond Penke ◽  
...  
Keyword(s):  
T Cell ◽  
T Cell Receptor ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Cell Receptor ◽  
Valeric Acid ◽  
Receptor Complex ◽  
Acid Labile

AbstractThe acid-labile 5-[(9-aminoxanthen-2-yl)oxy]valeric acid was prepared in a six-step route. The usefulness of the resulting handle was investigated with solid-phase peptide synthesis of cholecystokinin-8 sulfate and the phosphorylated fragment of the ζ-subunit of the T-cell receptor complex 138-144.

scholarly journals Revisiting NO2 as Protecting Group of Arginine in Solid-Phase Peptide Synthesis

2020 ◽  
Vol 21 (12) ◽  
pp. 4464
Author(s):  
Mahama Alhassan ◽  
Ashish Kumar ◽  
John Lopez ◽  
Fernando Albericio ◽  
Beatriz G. de la Torre
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Reaction ◽  
Reducing Agent ◽  
Protecting Groups ◽  
Side Chain ◽  
Protecting Group ◽  
Mild Acid

The protection of side-chain arginine in solid-phase peptide synthesis requires attention since current protecting groups have several drawbacks. Herein, the NO2 group, which is scarcely used, has been revisited. This work shows that it prevents the formation of δ-lactam, the most severe side-reaction during the incorporation of Arg. Moreover, it is stable in solution for long periods and can be removed in an easy-to-understand manner. Thus, this protecting group can be removed while the protected peptide is still anchored to the resin, with SnCl2 as reducing agent in mild acid conditions using 2-MeTHF as solvent at 55 °C. Furthermore, we demonstrate that sonochemistry can facilitate the removal of NO2 from multiple Arg-containing peptides.

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