A selective synthesis of 4-aminobiphenyl-N2-deoxyguanosine adducts.
A selective synthesis of N2-deoxyguanosine adducts derived from 4-aminobiphenyl (ABP) is described. The reactions of O2-trifluoromethylsulfonyl-O6-allyl-3',5'-O-bis(tert-butyldimethyl silyl)-2'- deoxyxanthosine with 3-amino-4-acetaminobiphenyl and 4-hydrazinobiphenyl, respectively, are the key steps. Successive removal of the protecting groups from the protected adducts leads to the free adducts 3-(deoxyguanosine-N2-yl)-acetyl-ABP and N-(deoxyguanosyl-N2-yl)-ABP, respectively.
Scheer
S
S
Fachbereich Chemie der Universitat, Marburg, Germany.
Steinbrecher
T
T
Boche
G
G
D000611:Aminobiphenyl Compounds / Q000138:chemical synthesis*; D002273:Carcinogens / Q000737:chemistry*; D018736:DNA Adducts / Q000138:chemical synthesis*; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D015394:Molecular Structure; D009153:Mutagens / Q000737:chemistry*
D000611:Aminobiphenyl Compounds; D002273:Carcinogens; D018736:DNA Adducts; D009153:Mutagens; C053420:N-(deoxyguanosin-8-yl)-4-aminobiphenyl; D003849:Deoxyguanosine