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Issue 27, 2019
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Full solid-phase total synthesis of macrocyclic natural peptides using four-dimensionally orthogonal protective groups

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Abstract

Fmoc-based solid-phase synthesis provides efficient access to both linear and macrocyclic peptides. To synthesize complex macrocyclic polyamides using Fmoc chemistry, multiple protective groups with orthogonal reactivities are generally employed because the free amines and carboxylic acids of specific residues must be selectively exposed prior to amide formation. This review focuses on four-dimensionally orthogonal protective group strategies for the full solid-phase synthesis of macrocyclic peptides with branched chains (polymyxin E2 and daptomycin) and a tricyclic natural peptide (lacticin 481).

Graphical abstract: Full solid-phase total synthesis of macrocyclic natural peptides using four-dimensionally orthogonal protective groups

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Publication details

The article was received on 15 May 2019, accepted on 15 Jun 2019 and first published on 17 Jun 2019


Article type: Review Article
DOI: 10.1039/C9OB01130G
Org. Biomol. Chem., 2019,17, 6519-6527

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    Full solid-phase total synthesis of macrocyclic natural peptides using four-dimensionally orthogonal protective groups

    H. Itoh and M. Inoue, Org. Biomol. Chem., 2019, 17, 6519
    DOI: 10.1039/C9OB01130G

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