title: Highly chemoselective ligation of thiol- and amino-peptides on a bromomaleimide core.
abstract: Application of a bromomaleimide core allows for the incorporation of three different peptides. The key reactions of the process are the selective stapling of both thiol- and amino-peptides on two different sites of the core. The thiol-peptide attacks and replaces the bromide whereas the amino-peptide attaches to the ene-position of the core revealing differential and selective reactivity. This platform will have further application in protein chemistry, multidrug presentation and vaccine preparation.
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa. beatrizgdelatorre@gmail.com.
authors.forename: Suhas
authors.initials: S
authors.lastname: Ramesh
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa. beatrizgdelatorre@gmail.com.
authors.forename: Prabhakar
authors.initials: P
authors.lastname: Cherkupally
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa. beatrizgdelatorre@gmail.com.
authors.forename: Thavendran
authors.initials: T
authors.lastname: Govender
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa. beatrizgdelatorre@gmail.com.
authors.forename: Hendrik G
authors.initials: HG
authors.lastname: Kruger
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa. beatrizgdelatorre@gmail.com and School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa. Albericio@ukzn.ac.za.
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.affiliation: Catalysis and Peptide Research Unit, School of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa. beatrizgdelatorre@gmail.com.
authors.forename: Beatriz G
authors.initials: BG
authors.lastname: de la Torre
mesh_terms: D000588:Amines / Q000378:metabolism*; D001966:Bromine / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008301:Maleimides / Q000378:metabolism*; D010455:Peptides / Q000378:metabolism*; D013438:Sulfhydryl Compounds / Q000378:metabolism*
chemical_list: D000588:Amines; D008301:Maleimides; D010455:Peptides; D013438:Sulfhydryl Compounds; C043592:maleimide; D001966:Bromine