A new protecting group for tryptophan in solid-phase peptide synthesis which protects against acid-catalyzed side reactions and facilitates purification by HPLC

2009 ◽  
Vol 50 (24) ◽  
pp. 2976-2978 ◽  
Author(s):  
Karolina Wahlström ◽  
Anders Undén
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Reactions ◽  
Protecting Group ◽  
Acid Catalyzed

scholarly journals Automated solid-phase peptide synthesis to obtain therapeutic peptides

2014 ◽  
Vol 10 ◽  
pp. 1197-1212 ◽  
Author(s):  
Veronika Mäde ◽  
Sylvia Els-Heindl ◽  
Annette G Beck-Sickinger
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Protecting Group ◽  
Drug Candidates ◽  
Tremendous Progress ◽  
Pharmacokinetic Properties ◽  
Critical Issues ◽  
Therapeutic Peptides ◽  
Automated Methods

The great versatility and the inherent high affinities of peptides for their respective targets have led to tremendous progress for therapeutic applications in the last years. In order to increase the drugability of these frequently unstable and rapidly cleared molecules, chemical modifications are of great interest. Automated solid-phase peptide synthesis (SPPS) offers a suitable technology to produce chemically engineered peptides. This review concentrates on the application of SPPS by Fmoc/t-Bu protecting-group strategy, which is most commonly used. Critical issues and suggestions for the synthesis are covered. The development of automated methods from conventional to essentially improved microwave-assisted instruments is discussed. In order to improve pharmacokinetic properties of peptides, lipidation and PEGylation are described as covalent conjugation methods, which can be applied by a combination of automated and manual synthesis approaches. The synthesis and application of SPPS is described for neuropeptide Y receptor analogs as an example for bioactive hormones. The applied strategies represent innovative and potent methods for the development of novel peptide drug candidates that can be manufactured with optimized automated synthesis technologies.

Pyruvoyl, a novel amino protecting group on the solid phase peptide synthesis and the peptide condensation reaction

2009 ◽  
Vol 50 (7) ◽  
pp. 818-821 ◽  
Author(s):  
Hidekazu Katayama ◽  
Takumi Utsumi ◽  
Chinatsu Ozawa ◽  
Yuko Nakahara ◽  
Hironobu Hojo ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Condensation Reaction ◽  
Solid Phase Peptide Synthesis ◽  
Protecting Group

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.

Sign in / Sign up

Export Citation Format

Share Document