Synthesis of the Antimicrobial S‐Linked Glycopeptide, Glycocin F

Abstract

The first total synthesis of glycocin F, a uniquely diglycosylated antimicrobial peptide bearing a rare S-linked N-acetylglucosamine (GlcNAc) moiety in addition to an O-linked GlcNAc, has been accomplished using a native chemical ligation strategy. The synthetic and naturally occurring peptides were compared by HPLC, mass spectrometry, NMR and CD spectroscopy, and their stability towards chymotrypsin digestion and antimicrobial activity were measured. This is the first comprehensive structural and functional comparison of a naturally occurring glycocin with an active synthetic analogue.

References

Page 1

	Year	Citations
Synthesis of Proteins by Native Chemical Ligation Philip E. Dawson, Tom W. Muir, Ian Clark‐Lewis, Science BiosynthesisEngineeringBiochemistryProtein FoldingNatural Sciences	1994	4.1K
Protein Chemical Synthesis by Ligation of Peptide Hydrazides Ge‐Min Fang, Yi‐Ming Li, Fei Shen, Angewandte Chemie International Edition	2011	779
Protein synthesis by native chemical ligation: Expanded scope by using straightforward methodology Tilman M. Hackeng, John H. Griffin, Philip E. Dawson Proceedings of the National Academy of Sciences	1999	664
Insights into the Mechanism and Catalysis of the Native Chemical Ligation Reaction Erik C. B. Johnson, Stephen B. H. Kent Journal of the American Chemical Society	2006	628
Chemical synthesis of proteins using peptide hydrazides as thioester surrogates Ji‐Shen Zheng, Shan Tang, Yun‐Kun Qi, Nature Protocols BiochemistryNatural SciencesPeptide EngineeringPeptide LibraryBioconjugation	2013	512
An Efficient Fmoc‐SPPS Approach for the Generation of Thioester Peptide Precursors for Use in Native Chemical Ligation Juan B. Blanco‐Canosa, Philip E. Dawson Angewandte Chemie International Edition	2008	505
Cysteine <i>S</i>-glycosylation, a new post-translational modification found in glycopeptide bacteriocins Judith Stepper, Shilpa Shastri, Trevor S. Loo, FEBS Letters	2011	159
Protein Chemical Synthesis by Ligation of Peptide Hydrazides Ge‐Min Fang, Yi‐Ming Li, Fei Shen, Angewandte Chemie	2011	147
Chemical Synthesis of an Erythropoietin Glycoform Containing a Complex‐type Disialyloligosaccharide Masumi Murakami, Ryo Okamoto, Masayuki Izumi, Angewandte Chemie International Edition Sialyloligosaccharyl-erythropoietin GlycoformBiosynthesisBioorganic ChemistryNew Reaction ConditionsBiochemistry	2012	142
An Efficient Fmoc‐SPPS Approach for the Generation of Thioester Peptide Precursors for Use in Native Chemical Ligation Juan B. Blanco‐Canosa, Philip E. Dawson Angewandte Chemie EngineeringPeptide EngineeringPeptide SciencePeptide TherapeuticsPeptide Chemistry	2008	114

Page 1