Abstract
This chapter describes variable success of peptide–resin cleavage and deprotection following solid-phase synthesis. Successful solid-phase peptide synthesis requires highly efficient assembly of a desired sequence and minimization of deleterious side-reactions that occur during assembly, side-chain deprotection, and cleavage. In a study described in the chapter, the reversed-phase high-performance liquid chromatography (RP-HPLC) retention time of the apparent, fully deprotected desired peptide was 8.69 ± 0.20 min, while that of the apparent Na-Fmoc desired peptide was 14.15 ± 0.15 min. RP-HPLC analyses indicated that 3 out of 12 Bocsynthesized crude products contained 25–75% of the desired peptide, while 25 out of 34 Fmoc-synthesized crude products contained 25–75% of the desired peptide. Twenty of the 46 products were compositionally correct by AAA compared with peptide standards, 18 from the Fmoc synthesis and 2 from the Boc synthesis. Samples generally had low values for Lys, His, and/or Asx.
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