Angelici Gaetano, Falini Giuseppe, Hofmann Hans-Jörg, Huster Daniel, Monari Magda, Tomasini Claudia
Dipartimento di Chimica "G. Ciamician", Alma Mater Studiorum Università di Bologna, Via Selmi 21, 40126 Bologna (Italy), Fax: (+39) 051-2099456.
Institute of Biochemistry, University of Leipzig, Brüderstraße 34, 04103 Leipzig (Germany).
Chemistry. 2009 Aug 10;15(32):8037-8048. doi: 10.1002/chem.200900185.
A series of oligomers of the type Boc-(L-Phe-D-Oxd)(n)-OBn (Boc = tert-butoxycarbonyl; Oxd = 4-methyl-5-carboxy oxazolidin-2-one; Bn = benzyl) were prepared for n = 2-5. The shortest oligomer, Boc-(L-Phe-D-Oxd)(2)-OBn, aggregates and forms a fiber-like material with an anti-parallel beta-sheet structure in which the oligopeptide units are connected to each other by only one intermolecular hydrogen bond. The longer oligomers exhibit structural heterogeneity. They start to organize into secondary structures by the formation of intramolecular hydrogen bonds at the pentamer level. Microscopy and diffraction of the oligomers indicated a crystalline character for only the shorter ones.
