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Cyclic glycopeptidomimetics through a versatile sugar-based scaffold
Authors:Maria Altamura  Elisa Dragoni  Angela Simona Infantino  Laura Legnani  Steve B. Ludbrook  Gloria Menchi  Lucio Toma  Cristina Nativi
Affiliation:1. Menarini Ricerche S.p.A., via dei Sette Santi 1, I-50131 Firenze, Italy;2. Dipartimento di Chimica Organica, Universita’ di Firenze, via della Lastruccia, 13-Polo Scientifico e Tecnologico, Sesto F.no, I-50019 Firenze, Italy;3. Dipartimento di Chimica Organica, Universita’ di Pavia, via Taramelli 10, I-27100 Pavia, Italy;4. Dept of Screening and Compound Profiling, GlaxoSmithKline R&D, New Frontiers Science Park, Harlow, Essex CM19 5AW, UK;5. CERM, Universita’ di Firenze, via Sacconi, 6-Polo Scientifico e Tecnologico, Sesto F.no, I-50019 Firenze, Italy
Abstract:Cyclic peptidomimetics are attracting structures to obtain a distinct, bioactive conformation. Even more attractive are sugar-containing cyclic peptidomimetics which present turn structures induced by the pyranose ring when incorporated in cyclic peptides. The use of a new and versatile saccharidic scaffold to achieve sugar-based peptidomimetics is here reported together with the successful synthesis of diastereomerically pure cyclic SAA peptidomimetics 15 and 16.
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