Interaction of porphyrin and sapphyrin macrocycles with nucleobases and nucleosides - Spectroscopic, quantum chemical and chromatographic investigation
K. Zaruba et al., Interaction of porphyrin and sapphyrin macrocycles with nucleobases and nucleosides - Spectroscopic, quantum chemical and chromatographic investigation, ANALYT CHIM, 437(1), 2001, pp. 39-53
Novel oligopyrrole macrocycle-based sorbents were prepared via amide covale
nt bonding of carboxylic acids of porphyrin and sapphyrin derivatives to 3-
aminopropyl silica. Covalent attachment of Cu(II)-tetraphenylporphyrin form
yl-derivative was performed by amine linkage. Prepared sorbents were charac
terized by Raman spectroscopy and elemental analysis. Retention behavior of
nucleobases and nucleosides was investigated by HPLC. UV-VIS and H-1 NMR t
itrations were used to study the role of oligopyrrol macrocyclic receptors
for selective recognition of adenine, cytosine, thymine and uracil and thei
r nucleoside forms. The spectroscopic results were compared with quantum ch
emical calculations at semiempirical level and with the data obtained by HP
LC measurements. Obtained data suggest that an aromatic pi-pi stacking inte
ractions govern the HPLC separation. A different behavior was found for pur
ine and pyrimidine bases. An introduction of Cu(II) into porphyrin macrocyc
le led to a dramatic increase of separation efficiency, probably due to an
increase of interaction energy. (C) 2001 Elsevier Science B.V. All rights r
eserved.