Solid-Phase Synthesis and Cyclative Cleavage of Quorum Sensing ­Depsipeptide Analogues by Acylphenyldiazene Activation

Abstract

Depsipeptide analogues of auto-inducing peptides (AIPs) from all four Staphylococcus aureus subgroups were prepared as panning reagents for in vitro antibody selection. Stepwise Fmoc solid-phase synthesis was used to prepare the linear precursors, which were cyclized without epimerization in a one-pot cleavage reaction following oxidation of the stable acylphenylhydrazine linkage to the reactive acylphenyldiazene.

AIP analogue - cyclic depsipeptide - cyclization - acyldiazene - quorum sensing

References and Notes

<A NAME="RS10005ST-1">1</A>

Present Address: Institute of Health Biosciences and Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Syo-machi, Tokushima-shi, 770-8505, Japan.

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Present Address: CS Bio Co., 20 Kelly Court, Menlo Park, CA 94025, USA.

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Solid-phase amino acid analysis was performed by Peptide Technologies (Gaithersburg, MD). Briefly, solid resin samples were subjected to 1:1 propionic acid-HCl (12 M) at 110 °C for 24 h, after which the hydrolyzate was derivatized with Marfey’s reagent and characterized by RP-HPLC.

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MS analysis of purified panning reagents: 1, [M + H]⁺ = 1160.5 (theor.)/1160.6 (obs.); 2, [M + H]⁺ = 1078.5 (theor.)/1078.4 (obs.); 3, [M + H]⁺ = 1018.5 (theor.)/1018.5 (obs.); 4, [M + H]⁺ = 1208.5 (theor.)/1208.7 (obs.).

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