Synthesis of Stylissamide B, a Pro‐Rich Cyclic Heptapeptide Isolated From the Marine Sponge Stylissa caribica

Synthesis of Stylissamide B, a Pro-Rich Cyclic Heptapeptide Isolated From the Marine Sponge Stylissa caribica

Stylissamide B was successfully synthesized for the first time using Fmoc-SPPS monitored using ReD-A method followed by cyclization in solution phase. The linear peptide, Pro-Pro-Ile-Tyr-Pro-Phe-Pro, was cyclized to form stylissamide B. It is noted that position of the Pro-Pro-Pro motif affects cyclization efficiency.

ABSTRACT

Stylissamide B was successfully synthesized for the first time using Fmoc solid-phase peptide synthesis (Fmoc-SPPS) followed by cyclization in solution phase. The Fmoc-SPPS process was monitored using the reversible detection method for amino groups (ReD-A method). The linear peptide, Pro-Pro-Ile-Tyr-Pro-Phe-Pro, was cyclized to form stylissamide B. The spectral data obtained were in agreement with previously reported literature, thereby confirming the reliability of the synthetic method.

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