Site-selective DNA alkylation of GG steps by naphthaldiimide derivatives possessing enantiomeric epoxide.
We have synthesized an enantiomeric pair of novel DNA alkylating agents consisting of a naphthaldiimide intercalator and a chiral epoxy side chain. These naphthaldiimide derivatives have high DNA binding affinity and selectively alkylate 5'G of the GG steps for (S)-epoxide and 3'G for (R)-epoxide.
Okamoto
A
A
Department of Synthetic Chemistry and Biological Chemistry, Faculty of Engineering, Kyoto University, and CREST, Japan Science and Technology Corporation, Kyoto 606-8501 Japan.
Nakamura
T
T
Yoshida
K
K
Nakatani
K
K
Saito
I
I
D000478:Alkylation; D001483:Base Sequence; D004247:DNA / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D007094:Imides / Q000737:chemistry*; D013237:Stereoisomerism
D004852:Epoxy Compounds; D007094:Imides; D004247:DNA