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

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Article

Manzor, Kim¹  o Proinsias, Keith²  Kelleher, Fintan¹ 

[1] Inst Technol Tallaght, Ctr Appl Sci Hlth, Mol Design & Synth Grp, Dublin 24, Ireland

[2] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

关键词: Nisin;    Thioamide;    Microwave-enhanced solid-phase peptide synthesis;    Lantibiotics;    Dehydroalanine;   

DOI  :  10.1016/j.tetlet.2017.06.052

来源: Elsevier

【 摘 要 】

A number of A-ring analogues of the lantibiotic nisin, containing replacements for the Dha residue 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 represents the first reported preparation of a lantibiotic ring fragment containing a thioamide link. (C) 2017 Elsevier Ltd. All rights reserved.

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