Protection by Conformationally Restricted Mobility: First Solid-Phase Synthesis of Triostin A

• Published in: Chemistry : a European journal Vol. 14; no. 15; pp. 4475 - 4478
• Main Authors: Tulla-Puche, Judit, Marcucci, Eleonora, Fermin, Manuel, Bayó-Puxan, Núria, Albericio, Fernando
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 19.05.2008; WILEY‐VCH Verlag; Wiley
• Subjects: Chemistry; Chemistry, Multidisciplinary; Chromatography, High Pressure Liquid - methods; Combinatorial Chemistry Techniques; conformation analysis; Molecular Conformation; peptides; Physical Sciences; protecting groups; Quinoxalines - chemical synthesis; Quinoxalines - chemistry; Science & Technology; solid-phase synthesis; Stereoisomerism; triostin; conformation analysis; ANALOGS; triostin; peptides; QUINOXALINE ANTIBIOTICS; ANTITUMOR-ACTIVITY; solid-phase synthesis; ECHINOMYCIN; protecting groups; SEQUENCE SPECIFICITY; DNA; DES-N-TETRAMETHYLTRIOSTIN; BIS-INTERCALATORS; PEPTIDE-SYNTHESIS; BINDING
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.200800372

Conformationally restricted mobility: The application of an efficient solid‐phase strategy based on protection by conformationally restricted mobility (see scheme) has allowed, for the first time, the synthesis and determination of the biological activity of the two triostin A conformers, which result from the isomerization cis/trans of the N‐methyl group of Cys. The most polar conformer showed the greatest inhibitory effect on cell growth.