A Shortcut to the Synthesis of Peptide Thioesters

Fmoc solid phase peptide synthesis of peptide thioesters by displacement of the cyclic urethane moiety obtained by the selective activation of C-terminal serine.

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Ca2+-mediated thiolysis of peptide–resin linkage as an option for preparing protected peptide thioesters

Tetrahedron Letters ◽

10.1016/j.tetlet.2008.04.081 ◽

2008 ◽

Vol 49 (24) ◽

pp. 3853-3857 ◽

Cited By ~ 1

Author(s):

Patrícia B. Proti ◽

M. Terêsa M. Miranda

Keyword(s):

Peptide Thioesters

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Preparation of Peptide Thioesters using Fmoc-Solid-Phase Peptide Synthesis and its Application to the Construction of a Template-Assembled Synthetic Protein (TASP)

Tetrahedron Letters ◽

10.1016/s0040-4039(97)01434-2 ◽

1997 ◽

Vol 38 (35) ◽

pp. 6237-6240 ◽

Cited By ~ 95

Author(s):

Shiroh Futaki ◽

Koji Sogawa ◽

Jun Maruyama ◽

Tomoko Asahara ◽

Mineo Niwa ◽

...

Keyword(s):

Peptide Synthesis ◽

Solid Phase ◽

Solid Phase Peptide Synthesis ◽

Synthetic Protein ◽

Peptide Thioesters

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Insights into the Mechanism and Catalysis of Peptide Thioester Synthesis by Alkylselenols Provide a New Tool for Chemical Protein Synthesis

Molecules ◽

10.3390/molecules26051386 ◽

2021 ◽

Vol 26 (5) ◽

pp. 1386

Author(s):

Florent Kerdraon ◽

Gemma Bogard ◽

Benoît Snella ◽

Hervé Drobecq ◽

Muriel Pichavant ◽

...

Keyword(s):

Protein Synthesis ◽

Total Synthesis ◽

Adaptive Immunity ◽

Biologically Active ◽

Acidic Ph ◽

Innate And Adaptive Immunity ◽

Chemotactic Protein ◽

Chemical Protein Synthesis ◽

Peptide Thioester ◽

Peptide Thioesters

While thiol-based catalysts are widely employed for chemical protein synthesis relying on peptide thioester chemistry, this is less true for selenol-based catalysts whose development is in its infancy. In this study, we compared different selenols derived from the selenocysteamine scaffold for their capacity to promote thiol–thioester exchanges in water at mildly acidic pH and the production of peptide thioesters from bis(2-sulfanylethyl)amido (SEA) peptides. The usefulness of a selected selenol compound is illustrated by the total synthesis of a biologically active human chemotactic protein, which plays an important role in innate and adaptive immunity.

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