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A Fiberlike Peptide Material Stabilized by Single Intermolecular Hydrogen Bonds
Author(s) -
Angelici Gaetano,
Falini Giuseppe,
Hofmann HansJörg,
Huster Daniel,
Monari Magda,
Tomasini Claudia
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200802587
Subject(s) - dipeptide , intermolecular force , hydrogen bond , chemistry , phenylalanine , peptide , beta sheet , stereochemistry , crystallography , organic chemistry , molecule , amino acid , biochemistry
One is enough : The dipeptide Boc‐ L ‐Phe‐ D ‐Oxd‐OBn (Boc= tert ‐butoxycarbonyl, Phe=phenylalanine, Oxd=4‐methyl‐5‐carboxy oxazolidin‐2‐one, Bn=benzyl; see picture; gray C, white H, red O, blue N) spontaneously forms uniform fibers consisting of parallel infinite linear chains arising from single intermolecular NH⋅⋅⋅OC hydrogen bonds. This is the absolute borderline case of a parallel β‐sheet structure.