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Stereoselective Formation of Chiral Metallopeptides
Author(s) -
Rama Gustavo,
Ardá Ana,
Maréchal JeanDidier,
Gamba Ilaria,
Ishida Hitoshi,
JiménezBarbero Jesús,
Vázquez M. Eugenio,
Vázquez López Miguel
Publication year - 2012
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.201201036
Subject(s) - chirality (physics) , circular dichroism , residue (chemistry) , stereoselectivity , proline , chemistry , stereochemistry , combinatorial chemistry , amino acid , aqueous solution , organic chemistry , physics , catalysis , biochemistry , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
Playing into our hands : The achiral bipyridine amino acid fluorenylmethyloxycarbonyl 5‐amino‐3‐oxapentanoic acid (Fmoc‐O1PenBpy‐OH) has been used for the solid‐phase synthesis of metallopeptides. Circular dichroism, molecular modeling, and NMR spectroscopic studies show that the chirality of the resulting metal complexes in aqueous solution is determined, and can thus be controlled, by the stereochemistry of one proline residue in the loop between the two coordinating O1PenBpy residues.