title: Soluble peptidyl phosphoranes for metal-free, stereoselective ligations in organic and aqueous solution.
abstract: Protocols for solid-phase syntheses of soluble peptidyl phosphoranes are presented. Various supported phosphoranylidene acetates were prepared on Rink amide or via alkylation of trialkyl- and triarylphosphines with bromoacetyl Wang ester. C-Acylation was conducted racemization-free with activated Fmoc-amino acids, followed by SPPS (solid-phase peptide synthesis). Acidic conditions released decarboxylated peptidyl phosphoranes into solution. The protocol allowed for the electronic variation of peptidyl phosphoranes which were investigated in ligation reactions with azides in organic and aqueous solvents.
authors.affiliation: Leibniz Institute of Molecular Pharmacology (FMP), Robert-Rössle-Strasse 10, 13125 Berlin, Germany.
authors.lastname: Ahsanullah
authors.forename: Samer I
authors.initials: SI
authors.lastname: Al-Gharabli
authors.forename: Jörg
authors.initials: J
authors.lastname: Rademann
mesh_terms: D000215:Acylation; D001386:Azides / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D010753:Phosphoranes / Q000138:chemical synthesis*; D012996:Solutions / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001386:Azides; D010455:Peptides; D010753:Phosphoranes; D012996:Solutions; D012997:Solvents