title: Chemical and enzymatic incorporation of N2-(p-n-butylphenyl)-2'-deoxyguanosine into an oligodeoxyribonucleotide.
abstract: An 18mer oligodeoxyribonucleotide containing a N2-(p-n-butylphenyl)-2'-deoxyguanosine (BuPdG) residue at the 3' end has been synthesized by both chemical and enzymatic methods. Chemical synthesis involved attachment of 5'-DMT-BuPdG as the 3'-H-phosphonate to uridine-controlled pore glass (CPG), followed by extension via H-phosphonate chemistry. After oxidation of the backbone, deprotection of bases, and removal from CPG, the uridine residue was removed by periodate cleavage and beta-elimination. The resulting oligomer 3'-phosphate was digested with alkaline phosphatase to give the free BuPdG-18mer. E.coli DNA polymerase I (Klenow) incorporated BuPdGTP at the 3' end of the corresponding 17mer primer annealed to a complementary 29mer template, and the properties of this product were identical to those of chemically synthesized BuPdG-18mer. E.coli DNA polymerase I (Klenow) was unable to extend the BuPdG-18mer, and the 3' to 5' exonuclease activity of the enzyme was unable to remove the modified nucleotide.
authors.affiliation: Department of Pharmacology, University of Massachusetts Medical School, Worcester 01655.
authors.forename: H K
authors.initials: HK
authors.lastname: Misra
authors.forename: N N
authors.initials: NN
authors.lastname: Khan
authors.forename: S
authors.initials: S
authors.lastname: Agrawal
authors.forename: G E
authors.initials: GE
authors.lastname: Wright
mesh_terms: D001483:Base Sequence; D004256:DNA Polymerase I / Q000378:metabolism*; D004257:DNA Polymerase II / Q000037:antagonists & inhibitors*; D003848:Deoxyguanine Nucleotides / Q000378:metabolism; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000378:metabolism; D004926:Escherichia coli / Q000201:enzymology; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000096:biosynthesis* / Q000138:chemical synthesis*
chemical_list: D003848:Deoxyguanine Nucleotides; D009838:Oligodeoxyribonucleotides; C040363:N(2)-(4-n-butylphenyl) 2'-deoxyguanosine; C029603:deoxyguanosine triphosphate; D004256:DNA Polymerase I; D004257:DNA Polymerase II; D003849:Deoxyguanosine