Issue 27, 2019

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

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

Article information

Article type
Review Article
Submitted
15 may 2019
Accepted
15 iyn 2019
First published
17 iyn 2019

Org. Biomol. Chem., 2019,17, 6519-6527

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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