Synthesis of Peptides Containing Overlapping Lanthionine Bridges on the Solid Phase: An Analogue of Rings D and E of the Lantibiotic Nisin

Citations Over TimeTop 12% of 2011 papers

Abstract

A methodology for the solid-phase synthesis of the overlapping lanthionine bridges found in many lantibiotics has been developed. A novel Teoc/TMSE-protected lanthionine derivative has been synthesized, and this lanthionine, and an Aloc/allyl-protected lanthionine derivative, have been incorporated into a linear peptide using solid-phase peptide synthesis. Selective deprotection of the silyl protecting groups, followed by sequential cyclization, deprotection of the allyl protecting groups, and further cyclization, enabled the regioselective formation of an analogue of rings D and E of nisin.

Related Papers

• → Total synthesis of peptide antibiotic nisin(1988)69 cited
• → Structure and Biological Activity of Chemically Modified Nisin A Species(1996)52 cited
• → The Molecular Biology of Nisin and Its Structural Analogues(1993)14 cited
• → Ring-opening reactions for the solid-phase synthesis of nisin lipopeptide analogues(2022)1 cited
• Semi-synthesis of nisin-based peptide antibiotics(2013)