Side Reactions in Peptide Synthesis: Failure of Coupling in Solid-Phase Automatic Synthesis of a Fragment (Sequence 65-74) of the Acyl Carrier Protein

Abstract

Two major side-products and a desired peptide (each was one-third) were found in analysis of a synthesized fragment (65-74) of the acyl carrier protein by a solid-phase automatic peptide synthesizer. The peptide mixtures were separated and collected by HPLC. Each isolated peptide was characterized via amino-acid composition analysis, mass spectra and specific peptide-bond cleavage to prove the sequence. Each by-product had one amino-acid missing (72Ile and 73Asn, respectively) from the sequence of ACP(65-74).