Solid-Phase Synthesis of Difficult Peptide Sequences at Elevated Temperatures: A Critical Comparison of Microwave and Conventional Heating Technologies

• Published in: Journal of organic chemistry Vol. 73; no. 19; pp. 7532 - 7542
• Main Authors: Bacsa, Bernadett, Horváti, Kata, Bõsze, Szilvia, Andreae, Fritz, Kappe, C. Oliver
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 03.10.2008; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Cross-Linking Reagents; Electromagnetic Fields; Exact sciences and technology; Heating; Microwaves; Organic chemistry; Peptides; Peptides - chemical synthesis; Physical Sciences; Preparations and properties; Science & Technology; Temperature; ASSISTED SYNTHESIS; RESIN; IRRADIATION; AMINO-ACID; OPTIMIZED SYNTHESIS; N-ACYL; BUILDING-BLOCKS; EFFICIENT SYNTHESIS; COUPLING REAGENTS; PARALLEL SYNTHESIS; Benzotriazole derivatives; Peptides; Nitrogen heterocycle; Deprotection; Temperature effect; Microwave; Purity; Racemization; High temperature; Thermal reaction; Microwave heating; Carbodiimides; Styrene derivative polymer; Aminoacid; Peptide synthesis; Solid phase; Chemical synthesis

The Fmoc/t-Bu solid-phase synthesis of three difficult peptide sequences (a 9-mer, 15-mer, and 24-mer) was performed using N,N′-diisopropylcarbodiimide/1-hydroxybenzotriazole as coupling reagent on polystyrene, Tentagel, and ChemMatrix resins. In order to obtain an insight into the specific role of...