Soluble peptidyl-phosphoranes for metal-free, stereoselective ligations in organic and aqueous solution

Ahsanullah, S. I. Al-Gharabli, J. Rademann – 2012

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.

Titel
Soluble peptidyl-phosphoranes for metal-free, stereoselective ligations in organic and aqueous solution
Verfasser
Ahsanullah, S. I. Al-Gharabli, J. Rademann
Datum
2012
Kennung
DOI: 10.1021/ol202627h
Quelle/n
Zitierweise
Org. Lett, 2012, 14, 14-17
Art
Text
dfg_logo