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

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

Research output: Contribution to journal › Article › peer-review

45 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1910-1913
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	7
DOIs	https://doi.org/10.1021/ol300557g
Publication status	Published - Apr 6 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol300557g

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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.",

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AU - Hsieh, Yves S.Y.

AU - Wilkinson, Brendan L.

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AU - MacKay, Joel P.

AU - Matthews, Jacqueline M.

AU - Payne, Richard J.

PY - 2012/4/6

Y1 - 2012/4/6

N2 - 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.

AB - 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.

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

Abstract

ASJC Scopus subject areas

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