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Fullerene Unsymmetrical Bis‐Adducts as Models for Novel Peptidomimetics
Author(s) -
Milic Dragana,
Prato Maurizio
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900791
Subject(s) - chemistry , peptidomimetic , adduct , fullerene , mass spectrometry , peptide , nuclear magnetic resonance spectroscopy , amino acid , stereochemistry , formaldehyde , combinatorial chemistry , medicinal chemistry , organic chemistry , chromatography , biochemistry
Two classes of unsymmetrical, orthogonally protected bis‐fulleropyrrolidine amino acids have been prepared as models for fullerene‐based peptidomimetics with the carbon sphere inserted into the peptide backbone. Two successive [3+2]cycloadditions of azomethine ylides (thermally generated from formaldehyde and the corresponding orthogonally protected glycino‐amines and ‐acids) to C 60 afforded NHFmoc/CO 2 t Bu and NHBoc/CO 2 Me fulleropyrrolidine couples, offering the possibility of selective deprotection under both acidic and basic conditions. In both classes of unsymmetrical bis‐adducts, the distribution of all the trans ( t 1 – t 4 ) and equatorial ( e′ and e″ ) isomers was quite similar except for the t 3 NHBoc/CO 2 Me compound, which rapidly decomposed during chromatography. All compounds were characterized by UV/Vis, 1 H and 13 C NMR spectroscopy, and mass spectrometry.