Synthesis of adducts of o-quinone metabolites of carcinogenic polycyclic aromatic hydrocarbons with 2'-deoxyribonucleosides.
[structure: see text] The first syntheses of the adducts formed in the reactions of o-quinone metabolites of carcinogenic polycyclic aromatic hydrocarbons (BPQ and BAQ) at 2'-deoxyadenosine and 2'-deoxyguanosine sites in DNA are reported. These syntheses entail Pd-catalyzed coupling of protected amine derivatives of catechols with suitably protected halopurine analogues of 2'-deoxyribonucleosides.
Dai
Qing
Q
Ben May Institute for Cancer Research, The University of Chicago, Chicago, Illinois 60637, USA.
Ran
Chongzhao
C
Harvey
Ronald G
RG
D002273:Carcinogens / Q000737:chemistry*; D002384:Catalysis; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry
D002273:Carcinogens; D003853:Deoxyribonucleosides; D007202:Indicators and Reagents; D011084:Polycyclic Aromatic Hydrocarbons; D011809:Quinones