Solid-Phase Peptide Synthesis of Analogues of the N-Terminus A-ring Fragment of the Lantibiotic Nisin: Replacements for the Dehydroalanine (Dha) Residue at Position 5 and the First Incorporation of a Thioamide Residue

Authors

Kim Manzor, Institute of Technology Tallaght
Keith Ó Proinsias, Polish Academy of Sciences, Institute of Organic Chemistry
Fintan Kelleher, Technological University DublinFollow

Document Type

Article

Rights

Available under a Creative Commons Attribution Non-Commercial Share Alike 4.0 International Licence

Disciplines

Organic Chemistry, Microbiology

Publication Details

Tetrahedron Letters

DOI: 10.1016/j.tetlet.2017.06.052

Abstract

A number of A-ring analogues of the lantibiotic nisin, containing replacements for the Dha at position 5, have been successfully prepared by solid-phase peptide synthesis. The Dha replacements include glycine, alanine, phenylalanine, serine and 1-aminocyclopropyl carboxylic acid (ACCa). The incorporation of a thioamide-isoleucine residue at position 4 is also described and is the first report of the preparation of a lantibiotic ring fragment containing a thioamide link.

DOI

https://doi.org/10.1016/j.tetlet.2017.06.052

Recommended Citation

Manzor, K., O'Proinsias, K. & Kelleher, F. (2017) Solid-Phase Peptide Synthesis of Analogues of the N-Terminus A-ring Fragment of the Lantibiotic Nisin: Replacements for the Dehydroalanine (Dha) Residue at Position 5 and the First Incorporation of a Thioamide Residue, Tetrahedron Letters, DOI: 10.1016/j.tetlet.2017.06.052

Funder

Science Foundation Ireland