Tetrahydropyranyl and Tetrahydrofuranyl as New Backbone Protecting Groups For Enhanced Fmoc SPPS

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Acidic Cleavage Deprotection KineticsTHP and THF protected dipeptides with general structure Fmoc-Gly-(PG)Gly-OH, were reacted in cleavage solutions containing various amounts of TFA, monitored over a 3-hour period. They were compared to the Dmb group and a pseudoproline (Ser(ψ Me,Me Pro)) * motif.Results:• Tetrahydrofuran (THF) is hyper acid-labile• Tetrahydropyran (THP) can be removed in mild cleavage cocktails • Order of reactivity; THF > ψ Me,Me Pro > THP > Dmb

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