title: Solid-phase synthesis of succinylhydroxamate peptides: functionalized matrix metalloproteinase inhibitors.
abstract: [reaction: see text] A novel solid-phase synthesis strategy toward succinylhydroxamate peptides, using an appropriately protected hydroxamate building block, is described. Rapid and efficient access is gained to amine-functionalized peptides, which can be decorated with, for instance, a fluorescent label. In addition, we demonstrate an on-resin synthesis of a biotinylated photoactivatable hydroxamate peptide, which can be used as an activity-based probe for matrix metalloproteinases and ADAMs.
authors.affiliation: Department of Bio-organic Synthesis, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Michiel A
authors.initials: MA
authors.lastname: Leeuwenburgh
authors.forename: Paul P
authors.initials: PP
authors.lastname: Geurink
authors.forename: Theo
authors.initials: T
authors.lastname: Klein
authors.forename: Henk F
authors.initials: HF
authors.lastname: Kauffman
authors.forename: Gijs A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Rainer
authors.initials: R
authors.lastname: Bischoff
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
mesh_terms: D051722:ADAM Proteins / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005456:Fluorescent Dyes / Q000737:chemistry; D006877:Hydroxamic Acids / Q000138:chemical synthesis*; D008666:Metalloendopeptidases / Q000037:antagonists & inhibitors*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*; D013386:Succinates / Q000138:chemical synthesis*
chemical_list: D004791:Enzyme Inhibitors; D005456:Fluorescent Dyes; D006877:Hydroxamic Acids; D010455:Peptides; D013386:Succinates; D051722:ADAM Proteins; D008666:Metalloendopeptidases