title: Chiral discrimination in binding of enantiomers of 2-(aminoalkoxy)-substituted 4-(2-thienyl)pyrimidines and 4,6-bis(2-thienyl)pyrimidines with duplex DNA.
abstract: Thienylpyrimidines substituted at position 2 of the pyrimidine with a chiral aminoalkoxy group were synthesized. Upon interaction with duplex DNA, the unfused heteroaromatic system of these compounds intercalates with DNA base pairs and the protonated side chain is located in the major groove. The S-enantiomers bind more strongly than their R-counterparts with enantiomeric discrimination, as measured by a ratio of binding constants K(S)/K(R), ranging from 1.2 to 2.4.
authors.affiliation: Department of Chemistry, Georgia State University, Atlanta, 0302-4098, USA. lucjan@gsu.edu
authors.forename: Lucjan
authors.initials: L
authors.lastname: Strekowski
authors.forename: Marek T
authors.initials: MT
authors.lastname: Cegla
authors.forename: Vidya
authors.initials: V
authors.lastname: Honkan
authors.forename: Henryk
authors.initials: H
authors.lastname: Buczak
authors.forename: W Rucks
authors.initials: WR
authors.lastname: Winkeljohn
authors.forename: Alfons L
authors.initials: AL
authors.lastname: Baumstark
authors.forename: W David
authors.initials: WD
authors.lastname: Wilson
mesh_terms: D004247:DNA / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D011743:Pyrimidines; D004247:DNA