Total synthesis of a depsidomycin analogue by convergent solid-phase peptide synthesis and macrolactonization strategy for antitubercular activity

2011 ◽  
Vol 17 (10) ◽  
pp. 683-689 ◽  
Author(s):  
Venugopala K. Narayanaswamy ◽  
Fernando Albericio ◽  
Yacoob Mohamed Coovadia ◽  
Hendrik G. Kruger ◽  
Glenn E. M. Maguire ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Antitubercular Activity

scholarly journals Efficient and Reproducible Synthesis of an Fmoc-protected Tn Antigen

2021 ◽  
Author(s):  
Michael R. Reynolds ◽  
Sabrina Piazza ◽  
Jonathan Chiaramonte ◽  
Fabiola A. Chapa-Villarreal ◽  
John Trant
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Building Block ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Tn Antigen ◽  
Palladium Catalyzed ◽  
Glycosyl Donor ◽  
Antigen A

The total synthesis of the Thomsen-nouveau (Tn) antigen, a tumour-associated O-linked mucin glycopeptide, was achieved through a concise route. The key glycosylation step proved challenging to reproduce from the literature precedents and was most reliably accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-functionalized serine acceptor to form the target in moderate yields. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

Total synthesis of teixobactin and its stereoisomers

2018 ◽  
Vol 5 (9) ◽  
pp. 1431-1435 ◽  
Author(s):  
L. Liu ◽  
S. Wu ◽  
Q. Wang ◽  
M. Zhang ◽  
B. Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Total Syntheses ◽  
Combined Strategy

The total syntheses of teixobactin and a series of its stereoisomers at positions 2, 5, 6, 10 and 11 were achieved via a combined strategy of solution and solid phase peptide synthesis.

scholarly journals Efficient and Reproducible Synthesis of an Fmoc-protected Tn Antigen

2021 ◽  
Author(s):  
Michael R. Reynolds ◽  
Sabrina Piazza ◽  
Jonathan Chiaramonte ◽  
Fabiola A. Chapa-Villarreal ◽  
John Trant
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Building Block ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Tn Antigen ◽  
Palladium Catalyzed ◽  
Glycosyl Donor ◽  
Antigen A

The total synthesis of the Thomsen-nouveau (Tn) antigen, a tumour-associated O-linked mucin glycopeptide, was achieved through a concise route. The key glycosylation step proved challenging to reproduce from the literature precedents and was most reliably accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-functionalized serine acceptor to form the target in moderate yields. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

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.

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