Synthesis and biological activity of oxa-lacticin A2, a lantibiotic analogue with sulfur replaced by oxygen

Organic Letters
Hongqiang LiuJohn C Vederas

Abstract

An oxidatively stable analogue 3 of lacticin 3147 A2 (2), wherein the sulfur atoms are replaced with oxygens, was synthesized using solution phase peptide synthesis and sequential on-resin cyclizations. Biological evaluation suggests that oxa-lacticin A2 (3) retains independent antimicrobial activity against Gram-positive bacteria but lacks the synergistic activity with natural lacticin A1 that is characteristic of the native lacticin A2 peptide.

References

May 12, 2001·FEMS Microbiology Reviews·O McAuliffeC Hill
Jan 11, 2005·Current Protein & Peptide Science·Paul D CotterR Paul Ross
Feb 11, 2005·Chemical Reviews·Champak ChatterjeeWilfred A van der Donk
Mar 25, 2005·The Journal of Organic Chemistry·Sarah Bregant, Alethea B Tabor
Mar 15, 2006·Nature Reviews. Drug Discovery·Eefjan Breukink, Ben de Kruijff
Mar 23, 2007·Organic & Biomolecular Chemistry·Steven L Cobb, John C Vederas
May 18, 2007·Annual Review of Microbiology·Joanne M Willey, Wilfred A van der Donk
Jan 29, 2008·Mini Reviews in Medicinal Chemistry·Elaine M LawtonPaul D Cotter
Dec 31, 2008·Applied and Environmental Microbiology·Shawanda Wilson-StanfordLeif Smith

❮ Previous
Next ❯

Citations

Mar 13, 2012·Annual Review of Biochemistry·Patrick J Knerr, Wilfred A van der Donk
May 26, 2015·Expert Opinion on Drug Discovery·Jerome Escano, Leif Smith
Jun 12, 2012·Expert Opinion on Drug Discovery·Manuel Montalbán-LópezOscar P Kuipers
Nov 3, 2015·Biochimica Et Biophysica Acta·Sabine F OppedijkEefjan Breukink
Jun 9, 2016·Microbial Cell Factories·Elvis Legala Ongey, Peter Neubauer
Feb 13, 2019·Chembiochem : a European Journal of Chemical Biology·Arvind S SoniMartin E Tanner
Oct 1, 2011·Organic & Biomolecular Chemistry·Alethea B Tabor
Aug 19, 2011·Journal of the American Chemical Society·Wei LiuJohn C Vederas
Apr 30, 2013·Journal of the American Chemical Society·Patrick J Knerr, Wilfred A van der Donk
Nov 23, 2017·Journal of the American Chemical Society·Alireza BakhtiaryJohn C Vederas
Jan 28, 2012·Journal of the American Chemical Society·Avena C RossJohn C Vederas

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.