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    188宝金博页面版: A novel guanine N3 alkylation by antitumor antibiotic duocarmycin A

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    内容提示： Temtmkan Lams, Vol. 34. No. 13. PP. 2179-2182.1993 -m s6.w+LlD FGlUdiU~BIiti PcrpxmPrasLtd ‘. . . ANOVEL GUNINE N3 ALEYLA’ITONBYANTlTUMORANTIBICWIC ’ DUOC-CWA Hiroshi Sugiyama*, Kazuahige Ohmori, Kit Lam Ghan, J&aahiro HO&R, Akira Ad, Hiromipu &it.& and Isa0 Saito* : ,Department of Synthetic Chemistry, Faculty of weering, -to University, Kyoto &1)6, Japan *okyo Reseaxh Laboratoriee, Kyo~~kko Kogyo, Co., Lt& Machida, Tokyo 194, Key Worda DNA alkylation; duocarmycin A Abdract: Antitumor antibiotic duocamy...

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    Temtmkan Lams, Vol. 34. No. 13. PP. 2179-2182.1993 -m s6.w+LlD FGlUdiU~BIiti PcrpxmPrasLtd ‘. . . ANOVEL GUNINE N3 ALEYLA’ITONBYANTlTUMORANTIBICWIC ’ DUOC-CWA Hiroshi Sugiyama*, Kazuahige Ohmori, Kit Lam Ghan, J&aahiro HO&R, Akira Ad, Hiromipu &it.& and Isa0 Saito* : ,Department of Synthetic Chemistry, Faculty of weering, -to University, Kyoto &1)6, Japan *okyo Reseaxh Laboratoriee, Kyo~~kko Kogyo, Co., Lt& Machida, Tokyo 194, Key Worda DNA alkylation; duocarmycin A Abdract: Antitumor antibiotic duocamycin A wae bund tb undergo a novel N3 alkylat#on of thegucrnine residue .R$$ sf cuGckATTGc_)2. Guahe base wps shown ti be D semml m&r targetof duocamaycin A in DNA Sequence-specific DNA alkylation by antitumor antibiotics, duocarmycin A,1 CC-1063,s and their Bynthetic analogueeg has received much current attention. The heat-induced strand cleavage assay by ueing high resolution gel electrophoreeie has demon@rated that theee reagents aIkyIate the adenfne residues at the 3’ tide of the sequences of three or more consecutie A-T base pairs in double-stranded DNA.VV These reagenta epec&ally alkylate N3 of adenine base which is accessible in the minor groove of DNA By the use of synthetic aligonucleotide tiC1G~T&T&C7G&, we demonstrated that the cyclopropane subunit of duocarmycin A alkylates N3 of adeninw (&I to provide the covalent adduct which ia further decomposed to an abasic site-containing oligomer with concomitant release of duocarmycin A-adenine adduct 1 upon heating.lb We now wish to report herein a novel guanine N3 alkylation by duocarmycin A in the reactions with deoxyoctanucleotide~, and calf thymua DNA9 ’ % 2179

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