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Controllable Core―shell Type Resin for Solid-phase Peptide Synthesis
Hong-Jun Cho , Tae-Kyung Lee , Jung Won Kim , Sang-Myung Lee , and Yoon-Sik Lee
J. Org. Chem., Just Accepted Manuscript
DOI: 10.1021/jo301716d
Publication Date (Web): September 25, 2012
Copyright © 2012 American Chemical Society

A simple, mild and inexpensive bi-phasic functionalization approach is attempted for preparing an ideal core-shell type resin. The core-shell type architecture was constructed by coupling Fmoc-OSu to the amino groups on the shell layer of an aminomethyl polystyrene (AM PS) resin. The shell layer thickness of the resin could be easily controlled under mild conditions, which was characterized by Confocal Laser Scanning Microscopy (CLSM). The efficiency of core-shell type resin for solid-phase peptide synthesis (SPPS) was demonstrated by the synthesis of various peptides, and compared with commercially available non-coreshell type resins, such as AM PS and poly(ethylene glycol)-based resins. The coreshell type resin provided effective performance during the synthesis of hydrophobic peptide sequences, a disulfide-bridged cyclic peptide and a difficult PNA sequence. Furthermore, a highly aggregative peptide fragment, MoPrP 105–125, was synthesized more efficiently on the coreshell type resin under microwave condition than AM PS and ChemMatrix resins.