Direct Solid-Phase Synthesis of the β-Amyloid (1−42) Peptide Using Controlled Microwave Heating

• Published in: Journal of organic chemistry Vol. 75; no. 6; pp. 2103 - 2106
• Main Authors: Bacsa, Bernadett, Bősze, Szilvia, Kappe, C. Oliver
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 19.03.2010
• Subjects: Amino Acid Sequence; Amyloid beta-Peptides - chemical synthesis; Amyloid beta-Peptides - chemistry; Chemistry; Chromatography, High Pressure Liquid; Exact sciences and technology; Microwaves; Molecular Sequence Data; Molecular Structure; Organic chemistry; Peptide Fragments - chemical synthesis; Peptide Fragments - chemistry; Peptides; Peptides - chemical synthesis; Peptides - chemistry; Preparations and properties; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Benzotriazole derivatives; Chemical reagent; Peptides; Nitrogen heterocycle; Glycoprotein; Microwave; Racemization; Microwave heating; Protein; Aminoacid; Amyloid; Solid phase; Chemical synthesis; Room temperature
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo100136r

Standard linear Fmoc/t-Bu solid-phase synthesis of the 42-mer β-amyloid (1−42) peptide was achieved under controlled microwave conditions at 86 °C using inexpensive DIC/HOBt as coupling reagent on ChemMatrix resin. In order to avoid racemization of the sensitive amino acids, the coupling of the three His residues in the difficult peptide sequence was performed at room temperature. The desired peptide was obtained within 15 h overall processing time in high yield and purity (78% crude yield).