Chiral discrimination in binding of enantiomers of 2-(aminoalkoxy)-substituted 4-(2-thienyl)pyrimidines and 4,6-bis(2-thienyl)pyrimidines with duplex DNA.
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.
Strekowski
Lucjan
L
Department of Chemistry, Georgia State University, Atlanta, 0302-4098, USA. lucjan@gsu.edu
Cegla
Marek T
MT
Honkan
Vidya
V
Buczak
Henryk
H
Winkeljohn
W Rucks
WR
Baumstark
Alfons L
AL
Wilson
W David
WD
D004247:DNA / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000737:chemistry*; D013237:Stereoisomerism
D011743:Pyrimidines; D004247:DNA