Synthesis of the bacteriocin glycopeptide sublancin 168 and S-glycosylated variants

Yves S Y Hsieh; Brendan L Wilkinson; Mitchell R O'Connell; Joel P Mackay; Jacqueline M Matthews; Richard J Payne

doi:10.1021/ol300557g

Synthesis of the bacteriocin glycopeptide sublancin 168 and S-glycosylated variants

Org Lett. 2012 Apr 6;14(7):1910-3. doi: 10.1021/ol300557g. Epub 2012 Mar 28.

Authors

Yves S Y Hsieh¹, Brendan L Wilkinson, Mitchell R O'Connell, Joel P Mackay, Jacqueline M Matthews, Richard J Payne

Affiliation

¹ School of Chemistry, The University of Sydney, NSW 2006, Australia.

PMID: 22455748
DOI: 10.1021/ol300557g

Abstract

The synthesis of sublancin 168, a unique S-glucosylated bacteriocin antibiotic, is described. The natural product and two S-glycosylated variants were successfully prepared via native chemical ligation followed by folding. The synthetic glycopeptides were shown to possess primarily an α-helical secondary structure by CD and NMR studies.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acid Sequence
Bacteriocins / chemical synthesis*
Bacteriocins / chemistry
Circular Dichroism
Glycopeptides / chemical synthesis*
Glycopeptides / chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular

Substances

Bacteriocins
Glycopeptides
sublancin 168