scholarly journals Protection of .PSI.(CH2NH) Peptide Bond with 2,4-Dimethoxybenzyl Group in Solid-Phase Peptide Synthesis.

1997 ◽  
Vol 45 (1) ◽  
pp. 13-17 ◽  
Author(s):  
Yusuke SASAKI ◽  
Junko ABE
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Bond

scholarly journals The 9-Fluorenylmethoxycarbonyl (Fmoc) Group in Chemical Peptide Synthesis – Its Past, Present, and Future

2020 ◽  
Vol 73 (4) ◽  
pp. 271 ◽  
Author(s):  
Wenyi Li ◽  
Neil M. O'Brien-Simpson ◽  
Mohammed Akhter Hossain ◽  
John D. Wade
Keyword(s):  
Chemical Synthesis ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Bond ◽  
Synthesis Methods ◽  
Protecting Group ◽  
Fmoc Group ◽  
The 1960S ◽  
The Many

The chemical formation of the peptide bond has long fascinated and challenged organic chemists. It requires not only the activation of the carboxyl group of an amino acid but also the protection of the Nα-amino group. The more than a century of continuous development of ever-improved protecting group chemistry has been married to dramatic advances in the chemical synthesis of peptides that, itself, was substantially enhanced by the development of solid-phase peptide synthesis by R. B. Merrifield in the 1960s. While the latter technology has continued to undergo further refinement and improvement in both its chemistry and automation, the development of the base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group and its integration into current synthesis methods is considered a major landmark in the history of the chemical synthesis of peptides. The many beneficial attributes of the Fmoc group, which have yet to be surpassed by any other Nα-protecting group, allow very rapid and highly efficient synthesis of peptides, including ones of significant size and complexity, making it an even more valuable resource for research in the post-genomic world. This review charts the development and use of this Nα-protecting group and its adaptation to address the need for more green chemical peptide synthesis processes.

scholarly journals Effect of Microwave Radiation on Enzymatic and Chemical Peptide Bond Synthesis on Solid Phase

2009 ◽  
Vol 2009 ◽  
pp. 1-4 ◽  
Author(s):  
Alessandra Basso ◽  
Loris Sinigoi ◽  
Lucia Gardossi ◽  
Sabine Flitsch
Keyword(s):  
Enzyme Activity ◽  
Reaction Kinetics ◽  
Microwave Radiation ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Bond ◽  
Chemical Coupling

Peptide bond synthesis was performed on PEGA beads under microwave radiations. Classical chemical coupling as well as thermolysin catalyzed synthesis was studied, and the effect of microwave radiations on reaction kinetics, beads' integrity, and enzyme activity was assessed. Results demonstrate that microwave radiations can be profitably exploited to improve reaction kinetics in solid phase peptide synthesis when both chemical and biocatalytic strategies are used.

A Strategy for Thioamide Incorporation During Fmoc Solid-Phase Peptide Synthesis with Robust Stereochemical Integrity

2019 ◽  
Author(s):  
luis camacho III ◽  
Bryan J. Lampkin ◽  
Brett VanVeller
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Chains ◽  
Amino Acid Side Chains ◽  
Peptide Elongation

We describe a method to protect the sensitive stereochemistry of the thioamide—in analogy to the protection of the functional groups of amino acid side chains—in order to preserve the thioamide moiety during peptide elongation.<br>

Analytical Methods for Solid Phase Peptide Synthesis

2004 ◽  
Vol 8 (4) ◽  
pp. 291-301 ◽  
Author(s):  
Giuseppina Sabatino ◽  
Mario Chelli ◽  
Alberto Brandi ◽  
Anna Papini
Keyword(s):  
Peptide Synthesis ◽  
Analytical Methods ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis

Fmoc Solid Phase Peptide Synthesis

1999 ◽  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Chain ◽  
Standard Approach ◽  
Side Chain ◽  
Complex Structures ◽  
Protein Conjugation ◽  
Chemoselective Ligation ◽  
Routine Production

In the years since the publication of Atherton and Sheppard's volume, the technique of Fmoc solid-phase peptide synthesis has matured considerably and is now the standard approach for the routine production of peptides. The basic problems outstanding at the time of publication of this earlier work have now been, for the most part, solved. As a result, innovators in the field have focussed their efforts to develop methodologies and chemistry for the synthesis of more complex structures. The focus of this new volume is much broader, and covers not only the essential procedures for the production of linear peptides but also more advanced techniques for preparing cyclic, side-chain modified, phospho- and glycopeptides. Many other methods also deserving attention have been included: convergent peptide synthesis; peptide-protein conjugation; chemoselective ligation; and chemoselective purification. The difficult preparation of cysteine and methionine-containing peptides is also covered, as well as methods for overcoming aggregation during peptide chain assembly and a survey of available automated instrumentation.

scholarly journals Cover Picture: Propylphosphonic Anhydride (T3P®) as Coupling Reagent for Solid‐Phase Peptide Synthesis (11/2021)

2021 ◽  
Vol 6 (11) ◽  
pp. 2648-2648
Author(s):  
Othman Al Musaimi ◽  
Richard Wisdom ◽  
Peter Talbiersky ◽  
Beatriz G. De La Torre ◽  
Fernando Albericio
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reagent

Synthesis of MUC1 Peptide and Glycopeptide Dendrimers

2009 ◽  
Vol 62 (10) ◽  
pp. 1339 ◽  
Author(s):  
Candy K. Y. Chun ◽  
Richard J. Payne
Keyword(s):  
Peptide Synthesis ◽  
Tandem Repeat ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Cycloaddition Reaction ◽  
Repeat Sequence ◽  
Tandem Repeat Sequence ◽  
Multiple Copies ◽  
Fmoc Strategy

Several dendrimers possessing multiple copies of peptides and glycopeptides belonging to the MUC1 eicosapeptide tandem repeat sequence have been prepared. Fmoc-strategy solid-phase peptide synthesis was used to construct the peptides and glycopeptides, which were conjugated to suitably functionalized dendrimer cores using the copper-catalyzed azide-alkyne cycloaddition reaction to produce multivalent peptide and glycopeptide dendrimers.

Synthesis of 2-hydroxyethylsulfonyl-methyl-substituted polystyrenes and their application in solid phase peptide synthesis

Tetrahedron ◽  
1976 ◽  
Vol 32 (9) ◽  
pp. 1069-1071 ◽  
Author(s):  
Godefridus I. Tesser ◽  
Jan T.W.A.R.M. Buis ◽  
Erik Th.M. Wolters ◽  
Elizabeth G.A.M. Bothé-Helmes
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis
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