Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis.

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Medicinal Chemistry

Background:

• Solid-phase peptide synthesis (SPPS) is crucial for creating peptides.
• Cyclic peptides possess unique biological activities and structural properties.
• Efficient and recyclable reagents are desirable for sustainable synthesis.

Purpose of the Study:

• To evaluate a novel hypervalent iodine(III) reagent system for peptide synthesis.
• To demonstrate the utility of FPID and (4-MeOC6H4)3P in SPPS and cyclic peptide synthesis.
• To synthesize biologically active peptides using this new methodology.

Main Methods:

• Application of the FPID/(4-MeOC6H4)3P reagent system in solid-phase peptide synthesis.
• Solution-phase peptide synthesis for the preparation of cyclic peptides.
• Characterization of synthesized peptides for biological activity.

Main Results:

• Successful synthesis of four biologically active peptides via SPPS.
• Efficient preparation of the cyclic heptapeptide pseudostellarin D.
• Demonstration of the ready regeneration and recyclability of the FPID reagent post-reaction.

Conclusions:

• The FPID/(4-MeOC6H4)3P system is a versatile and effective tool for both SPPS and cyclic peptide synthesis.
• This method offers a sustainable approach due to the reagent's recyclability.
• The synthesized peptides hold potential for further investigation in medicinal chemistry.