Tetrahedron letters2022,Vol.923.DOI:10.1016/j.tetlet.2022.153677

Total synthesis of the macrocyclic peptide stylopeptide II using oxime resin

Berube, Christopher Borgia, Alexandre Voyer, Normand
Tetrahedron letters2022,Vol.923.DOI:10.1016/j.tetlet.2022.153677

Total synthesis of the macrocyclic peptide stylopeptide II using oxime resin

Berube, Christopher 1Borgia, Alexandre Voyer, Normand
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作者信息

  • 1. Univ Laval
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Abstract

We report the first total synthesis of the macrocyclic decapeptide stylopeptide II (1), which was isolated from the Papua New Guinea marine sponge of the Hymeniacidon genus (formerly Stylotella sp). The methodology to synthesize this compound exploitsthe oxime resin as solid support and is highly efficient allowing the preparation of the macrocyclic decapeptide without a chromatographic purification step. Notably, stylopeptide II (1) was rapidly prepared at gram-scale without any detectable amounts of undesired side products that could have arisen from the coupling, deprotection, cyclization, epimerization and dimerization reactions. The methology is general and accelerates the large-scale synthesis of macrocyclic peptides. (c) 2022 Elsevier Ltd. All rights reserved.

Key words

Cyclic peptides/Oxime resin/Macrocycles/Macrocyclization/Proline-rich cyclic peptides/SOLID-PHASE SYNTHESIS/POLYMER-BOUND OXIME/GRAMICIDIN-S/SPONGE

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN:0040-4039
被引量1
参考文献量31
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