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

Akira Shigenaga; Jason A. Moss; Fawn T. Ashley; Gunnar F. Kaufmann; Kim D. Janda

doi:10.1055/s-2006-932468

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Synlett 2006(4): 0551-0554
DOI: 10.1055/s-2006-932468

LETTER

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

Akira Shigenaga, Jason A. Moss, Fawn T. Ashley, Gunnar F. Kaufmann, Kim D. Janda*
Departments of Chemistry and Immunology, The Skaggs Institute for Chemical Biology, and Worm Institute for Research and Medicine (WIRM), The Scripps Research Institute 10550 N, Torrey Pines Road, La Jolla, CA 92037, USA
e-Mail: kdjanda@scripps.edu;

Further Information

Publication History

Received 3 October 2005
Publication Date:
20 February 2006 (online)

Abstract
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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.

Key words

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

References and Notes

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1

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.

2

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

29

Hypogel is an oligo(ethylene glycol)-grafted PS-DVB resin commercially available from Rapp Polymere (Tübingen, Germany), and was used at a loading of 0.41 mmol/g.

33

Water was omitted from the final TFA deprotection conditions to eliminate the prospect of acid-catalyzed ester hydrolysis.

34

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.

35

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.).