An efficient mild acidolytic deprotection procedure for Boc/Bzl-based solid phase peptide synthesis

1990 ◽  
Vol 55 (7) ◽  
pp. 1792-1800 ◽  
Author(s):  
Rudolf Dölling ◽  
Peter Jeschke ◽  
Albrecht Otto ◽  
Jutta Eichler
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Benzyl Ester

Using the mild acidolytic deprotecting reagents 0.1M MSA or 0.1M TMSOTf in TFA in combination with PMB, which simultaneously accelerates the cleavage and acts as irreversible scavenger, the rate of cleavage of a model dipeptide from the appropriate Nα-Fmoc-dipeptidyl resin (polymer-bound benzyl ester, p-MBHA and BHA resin, respectively) was studied. The new deprotecting method was successfully applied to the synthesis of three Nα-halogenoacetyl modified octapeptides (I, II) and a 16-residue peptide (III). In all cases, the crude products were of the same quality as peptides obtained via the HF/10% anisole technique.

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.

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