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Solid-phase Synthesis of Cyclic Hexapeptides Wollamides A, B and Desotamide B

Solid-phase Synthesis of Cyclic Hexapeptides Wollamides A, B and Desotamide B

Lissa S Tsutsumi, Ghee T Tan, Dianqing Sun

Tetrahedron Lett. 2017 Jul 5;58(27):2675-2680.

PMID: 29129945

Abstract:

Solid-phase synthesis of antibacterial cyclohexapeptides including wollamides A, B and desotamide B has been developed. Briefly, the protected linear hexapeptides were assembled on 2-chlorotrityl chloride resin using standard Fmoc chemistry and diisopropylcarbodiimide/hydroxybenzotriazole coupling reagents, cleaved off-resin with hexafluoroisopropanol/dichloromethane to keep side-chain protecting groups intact, and cyclized in solution. Final global removal of all protecting groups using a cocktail of trifluoroacetic acid/triisopropylsilane/dichloromethane afforded the desired cyclic hexapeptides, which were characterized by 1H, 13C NMR, and HRMS. Subsequent investigation of macrocyclization parameters such as terminal residues, coupling reagents, and cyclization concentration revealed the optimized conditions for the synthesis of this class of cyclic hexapeptides.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP17877235	Triisopropylsilanol		17877-23-5	Price

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