Abstract
Solid-phase peptide synthesis (SPPS) in the N-to-C direction (inverse SPPS [1–4]) provides the synthetically versatile peptide C-terminal carboxyl group for further modification, which is particularly useful in synthesis of C-terminally modified peptide mimetics. As part of our ongoing program to find peptide mimetic protease and penicillin-binding protein inhibitors, a strategy for inverse SPPS based on amino acid t-butyl esters has been developed. A principle advantage of this approach is the commercial availability of suitably side chain protected amino acid t-butyl esters. Based on this strategy, peptide trifluoromethyl ketones and peptide aldehydes have also been prepared, as well as several peptide aldehyde derivatives. These results demonstrate the feasibility and utility of this approach for peptide mimetic synthesis.
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