title: One-Pot Ligation-Oxidative Deselenization at Selenocysteine and Selenocystine.
abstract: The use of native chemical ligation at selenocysteine (Sec) residues with peptide thioesters and additive-free selenocystine ligation with peptides bearing phenyl selenoesters, in concert with one-pot oxidative deselenization chemistry, is described. These approaches provide a simple and rapid method for accessing native peptides with serine in place of Sec at the ligation junction. The efficiency of both variants of the one-pot ligation-oxidative deselenization chemistry is probed through the synthesis of a MUC5AC-derived glycopeptide.
authors.affiliation: School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia.
authors.forename: Nicholas J
authors.initials: NJ
authors.lastname: Mitchell
authors.affiliation: School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia.
authors.forename: Sameer S
authors.initials: SS
authors.lastname: Kulkarni
authors.affiliation: School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia.
authors.forename: Lara R
authors.initials: LR
authors.lastname: Malins
authors.affiliation: School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia.
authors.forename: Siyao
authors.initials: S
authors.lastname: Wang
authors.affiliation: School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia.
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Payne
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003553:Cystine / Q000031:analogs & derivatives* / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D013058:Mass Spectrometry; D055271:Mucin 5AC / Q000737:chemistry; D016566:Organoselenium Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D017279:Selenocysteine / Q000737:chemistry*
chemical_list: D006020:Glycopeptides; C524678:MUC5AC protein, human; D055271:Mucin 5AC; D016566:Organoselenium Compounds; D017279:Selenocysteine; C009226:selenocystine; D003553:Cystine
keywords: glycopeptides; native chemical ligation; oxidative deselenization; peptides; synthesis