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Nanofibers from Oxazolidi‐2‐one Containing Hybrid Foldamers: What is the Right Molecular Size?
Author(s) -
Angelici Gaetano,
Falini Giuseppe,
Hofmann HansJörg,
Huster Daniel,
Monari Magda,
Tomasini Claudia
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900185
Subject(s) - pentamer , oligomer , intramolecular force , hydrogen bond , intermolecular force , chemistry , crystallography , nanofiber , oligopeptide , polymer chemistry , stereochemistry , materials science , peptide , molecule , nanotechnology , organic chemistry , biochemistry
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 β‐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.