A Redox-Sensitive Resin Linker for the Solid Phase Synthesis of C-Terminal Modified Peptides

Abstract

With the rapid development of combinatorial chemistry using solid phase synthesis, there is a great deal of interest in developing new solid phase linkers, which are stable during the solid phase synthesis process and yet readily cleavable under mild conditions. By taking advantage of a "trimethyl lock"-facilitated lactonization reaction, we have developed a redox-sensitive resin linker for the synthesis of C-terminal-modified peptides. The cleavage only requires mild reducing agents such as sodium hydrosulfite, which is not expected to cause any problem with the commonly seen organic functional groups. Using this new linker, three short peptides were synthesized with high isolated yields (70-90%). Such a linker could potentially be used for the synthesis of modified peptide libraries, which allows for the ready cleavage of the linker under mild conditions.

Recyclable Surfaces for Amine Conjugation Chemistry via Redox Reaction

“…Finally, the lactone ring of the dihydrocoumarin is known to undergo ring opening to regenerate the benzoquinone acid group under oxidative conditions via N-bromosuccinimide. 25 In this study, the repeated immobilization and release of (bio)molecules on the switchable surface were verified by fluorescent imaging and contact angle measurements.…”

Design, Synthesis, and Biological Evaluation of (E)-N-Aryl-2-arylethenesulfonamide Analogues as Potent and Orally Bioavailable Microtubule-Targeted Anticancer Agents

“…N-Bromosuccinimide ring opening reaction of 22 afforded the target compound 20 in moderate yields (Scheme 8). 28 …”

Synthesis and characterization of an electroactive surface that releases γ-aminobutyric acid (GABA)

“…Rabbit IgG (purified immunoglobulin reagent grade) and monoclonal anti-γ -aminobutyric acid (clone GB-69, abbreviation: anti-GABA) were purchased from Sigma, St. Louis, MO. GABA-OBu t [23], 2-[2-(2-undec-10-enyloxyethoxy)ethoxy]ethanamine 8 [24], 3 [22], and 7 [20][21][22] were prepared according to known methods.…”

“…1. The actual compound studied, 1, borrows from a biotin releasing surface recently reported by Hodneland and Mrksich [5], which in turn, built upon the earlier protecting group chemistry and the pro-drug approach developed by Carpino, Wang, and Borchardt [20][21][22]. Herein we describe the synthesis of 1 and the preparation of self-assembled monolayers (SAMs) of this material on gold surfaces.…”