A series of oligomers of the type Boc-(L-Phe-D-Oxd)n-OBn (Boc = tert-butoxycarbonyl; Oxd = 4-methyl-5carboxy 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 β-sheet struc- ture 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. © 2009 Wiley-VCH Verlag GmbH & Co.

Nanofibers from oxazolidi-2-one containing hybrid foldamers: what is the right molecular size?

ANGELICI, GAETANO;
2009

Abstract

A series of oligomers of the type Boc-(L-Phe-D-Oxd)n-OBn (Boc = tert-butoxycarbonyl; Oxd = 4-methyl-5carboxy 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 β-sheet struc- ture 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. © 2009 Wiley-VCH Verlag GmbH & Co.
Angelici, Gaetano; Falini, Giuseppe; Hofmann, Hans Jörg; Huster, Daniel; Monari, Magda; Tomasini, Claudia
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/837894
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