scholarly journals Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 4004 ◽  
Author(s):  
Ashish Kumar ◽  
Anamika Sharma ◽  
Beatriz G. de la Torre ◽  
Fernando Albericio
Keyword(s):  
Peptide Synthesis ◽  
Ring Opening ◽  
Solid Phase ◽  
Theoretical Calculations ◽  
Solid Phase Peptide Synthesis ◽  
Time Dependent ◽  
Green Solvent ◽  
Protecting Group ◽  
Fmoc Protecting Group

GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl piperidides by time-dependent monitoring using NMR. The results, corroborated by theoretical calculations, indicate that a solution of piperidines in GVL should be prepared daily for a better Fmoc removal.

Solid phase synthesis of α-amino squaric acid-containing peptides

RSC Advances ◽  
2014 ◽  
Vol 4 (92) ◽  
pp. 50639-50643 ◽  
Author(s):  
Kentaro Maeda ◽  
Yu-ichi Kiniwa ◽  
Yasufumi Ohfune ◽  
Shinichi Ishiguro ◽  
Koichi Suzuki ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
New Method ◽  
Squaric Acid ◽  
Protecting Group ◽  
Phase Synthesis ◽  
Group Strategy ◽  
Fmoc Protecting Group

A new method has been developed for the synthesis of 3-(1-aminoalkyl)-4-hydroxycyclobut-3-ene-1,2-dione [(α-amino squaric acid (α-Asq)]-containing peptides using solid phase peptide synthesis according to an Fmoc protecting group strategy.

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
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