Premium
Chiral Diaminodiamide Copper(II) Complexes for the Enantioselective Recognition of Amino Acids: Synthesis of the Ligands and Formation Constants
Author(s) -
Armani Elisabetta,
Marchelli Rosangela,
Dossena Arnaldo,
Casnati Giuseppe,
Dallavalle Francesco
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690818
Subject(s) - chemistry , enantioselective synthesis , copper , phenylalanine , amino acid , aqueous solution , stereochemistry , valine , alanine , medicinal chemistry , catalysis , organic chemistry , biochemistry
( S , S )‐ N , N ′ ‐Bis(aminoacyl)ethane‐ and ( S , S )‐ N , N ′ ‐bis(aminoacyl)propanediamines (AA‐NN‐2 and AA‐NN‐3, respectively, AA = alanine, phenylalanine, valine) were synthesized as the dihydrochlorides, and their complexes with Cu(II) studied potentiometrically. Since these ligands in the presence of Cu(II) are able to perform chiral resolution of D , L ‐dansylamino acids in HPLC (reversed phase), in a certain pH range (6.5–8.5), it is important to know the equilibria existing between ligands and copper in aqueous solution. For AA‐NN‐2, four species, CuLH 3+ , CuL 2+ , Cu 2 L 2 H −2 2+ , and CuLH −2 , were detected, whereas for AA‐NN‐3, only CuLH 3+ , CuL 2+ , and CuLH −2 were found. The aim is to find out which complexes may be involved in the recognition process.