The synergy of ChemMatrix resin and pseudoproline building blocks renders RANTES, a complex aggregated chemokine.
Traditionally, solid-phase synthesis has relied on polystyrene-based resins for the synthesis of all kinds of peptides. However, due to their high hydrophobicity, these resins have certain limitations, particularly in the synthesis of complex peptides, and in such cases, poly(ethylene glycol) (PEG)-based resins are often found to give superior results. Another powerful strategy for expediting the assembly of complex peptides is to employ pseudoproline dipeptides. These derivatives disrupt the interactions among chains that are usually the cause of poor coupling yields in aggregated sequences. Here we report on an efficient stepwise solid-phase synthesis of RANTES (1-68) by combining the advantages of the totally PEG-based ChemMatrix resin and pseudoproline dipeptides.
García-Martín
Fayna
F
Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain.
White
Peter
P
Steinauer
René
R
Côté
Simon
S
Tulla-Puche
Judit
J
Albericio
Fernando
F
D000595:Amino Acid Sequence; D018946:Chemokine CCL5 / Q000138:chemical synthesis*; D004151:Dipeptides / Q000737:chemistry; D006801:Humans; D008969:Molecular Sequence Data; D011137:Polystyrenes / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry*
D018946:Chemokine CCL5; D004151:Dipeptides; D011137:Polystyrenes; D013844:Thiazoles; C517863:aminomethyl-ChemMatrix resin; C505976:pseudoproline; D011392:Proline