Two-dimensional NMR studies on the anthramycin-d(ATGCAT)2 adduct.
Two-dimensional NMR experiments were performed on the adduct of anthramycin with d(ATGCAT)2 to obtain the assignments of the nucleotide base and sugar protons as well as the anthramycin protons. Anthramycin is covalently attached to a guanine 2-amino group, forming the d(ATamGCAT).d(ATGCAT) modified duplex. The anthramycin protons in the minor groove exhibit NOEs to several nucleotide protons. The network of anthramycin-nucleotide NOEs and the measurement of the 10-Hz coupling constant between the anthramycin H11 and H11a protons shows that anthramycin is covalently attached as the S stereoisomer at the anthramycin C11 position with the side chain of anthramycin oriented toward the 5' end of the modified strand. The NOE data show that the anthramycin-modified duplex is in a right-handed conformation with all bases in an anti conformation. Analysis of the J1'-2' coupling constants for the resolved H1' resonances shows that the S-type conformation of the sugars is highly preferred.
Krugh
T R
TR
Department of Chemistry, University of Rochester, New York 14627.
Graves
D E
DE
Stone
M P
MP
D000876:Anthramycin / Q000031:analogs & derivatives; D001570:Benzodiazepinones; D004247:DNA; D018736:DNA Adducts; D004338:Drug Combinations; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides
D001570:Benzodiazepinones; D018736:DNA Adducts; D004338:Drug Combinations; D009838:Oligodeoxyribonucleotides; C020204:anthramycin-DNA; D000876:Anthramycin; D004247:DNA