Nanofibers from oxazolidi-2-one containing hybrid foldamers: what is the right molecular size?
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.
Dipartimento di Chimica "G. Ciamician", Alma Mater Studiorum Università di Bologna, Via Selmi 21, 40126 Bologna (Italy), Fax: (+39) 051-2099456.
Gaetano
G
Angelici
Dipartimento di Chimica "G. Ciamician", Alma Mater Studiorum Università di Bologna, Via Selmi 21, 40126 Bologna (Italy), Fax: (+39) 051-2099456.
Giuseppe
G
Falini
Institute of Biochemistry, University of Leipzig, Brüderstraße 34, 04103 Leipzig (Germany).
Hans-Jörg
HJ
Hofmann
Institute of Medical Physics and Biophysics, University of Leipzig, Härtelstr. 16-18, 04107 Leipzig (Germany).
Daniel
D
Huster
Dipartimento di Chimica "G. Ciamician", Alma Mater Studiorum Università di Bologna, Via Selmi 21, 40126 Bologna (Italy), Fax: (+39) 051-2099456.
Magda
M
Monari
Dipartimento di Chimica "G. Ciamician", Alma Mater Studiorum Università di Bologna, Via Selmi 21, 40126 Bologna (Italy), Fax: (+39) 051-2099456.
Claudia
C
Tomasini
D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D049329:Nanostructures / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D010649:Phenylalanine / Q000737:chemistry
D009842:Oligopeptides; D023303:Oxazolidinones; D010649:Phenylalanine