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Cyclic azole-homologated peptides from Marine sponges

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Abstract

This review discusses the chemistry of cyclic azole-homologated peptides (AHPs) from the marine sponges, Theonella swinhoei, other Theonella species, Calyx spp. and Plakina jamaicensis. The origin, distribution of AHPs and molecular structure elucidations of AHPs are described followed by their biosynthesis, bioactivity, and synthetic efforts towards their total synthesis. Reports of partial and total synthesis of AHPs extend beyond peptide coupling reactions and include creative construction of the non-proteinogenic amino acid components, mainly the homologated heteroaromatic and α-keto-β-amino acids. A useful conclusion is drawn regarding AHPs: despite their rarity, exotic structures and the potent protease inhibitory properties of some members, their synthesis is under-developed and beckons solutions for outstanding problems towards their efficient assembly.

Graphical abstract: Cyclic azole-homologated peptides from Marine sponges

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Publication details

The article was received on 25 Oct 2017, accepted on 28 Nov 2017 and first published on 28 Nov 2017


Article type: Review Article
DOI: 10.1039/C7OB02628E
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Cyclic azole-homologated peptides from Marine sponges

    T. F. Molinski, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02628E

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