COVALENT ALKYLATION OF DNA WITH DUOCARMYCIN-A - IDENTIFICATION OF ABASIC SITE STRUCTURE

被引：104

作者：

SUGIYAMA, H

HOSODA, M

SAITO, I

ASAI, A

SAITO, H

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT SYNTHET CHEM,KYOTO 606,JAPAN

[2] KYOWA HAKKO KOGYO CO LTD,TOKYO RES LABS,TOKYO 194,JAPAN

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(00)97278-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylation of d(CGTATACG) by antitumor antibiotic duocarmycin A was investigated. It was found that N3 of adenine6 (A6) attacks the cyclopropane subunit of duocarmycin A to produce covalently alkylated adduct 5. Upon heating (90 °C, 5 min) the adduct 5 decomposed to modified oligomer 1 with concomitant release of adenine adduct 2. © 1990.

引用

页码：7197 / 7200

页数：4

共 13 条

[1] SEQUENCE-SPECIFIC CLEAVAGE OF DNA BY N-BROMOACETYLDISTAMYCIN - PRODUCT AND KINETIC ANALYSES
BAKER, BF
DERVAN, PB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) : 2700 - 2712
[2] SYNTHESIS AND PRELIMINARY EVALUATION OF AGENTS INCORPORATING THE PHARMACOPHORE OF THE DUOCARMYCIN PYRINDAMYCIN ALKYLATION SUBUNIT - IDENTIFICATION OF THE CC-1065 DUOCARMYCIN COMMON PHARMACOPHORE
BOGER, DL
ISHIZAKI, T
ZARRINMAYEH, H
KITOS, PA
SUNTORNWAT, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) : 4499 - 4502
[3] REACTION OF THE ANTITUMOR ANTIBIOTIC CC-1065 WITH DNA - STRUCTURE OF A DNA ADDUCT WITH DNA-SEQUENCE SPECIFICITY
HURLEY, LH
REYNOLDS, VL
SWENSON, DH
PETZOLD, GL
SCAHILL, TA
[J]. SCIENCE, 1984, 226 (4676) : 843 - 844
[4] DC89-A1, A NEW ANTITUMOR ANTIBIOTIC FROM STREPTOMYCES
ICHIMURA, M
MUROI, K
ASANO, K
KAWAMOTO, I
TOMITA, F
MORIMOTO, M
NAKANO, H
[J]. JOURNAL OF ANTIBIOTICS, 1988, 41 (09) : 1285 - 1288
[5] MILD ACID-HYDROLYSIS OF 2-PYRIMIDINONE-CONTAINING DNA FRAGMENTS GENERATES APURINIC APYRIMIDINIC SITES
IOCONO, JA
GILDEA, B
MCLAUGHLIN, LW
[J]. TETRAHEDRON LETTERS, 1990, 31 (02) : 175 - 178
[6] EFFICIENT, SPECIFIC CROSS-LINKING AND CLEAVAGE OF DNA BY STABLE, SYNTHETIC COMPLEMENTARY OLIGODEOXYNUCLEOTIDES
MEYER, RB
TABONE, JC
HURST, GD
SMITH, TM
GAMPER, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) : 8517 - 8519
[7] APPLICATION OF 2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORODIAMIDITE FOR INSITU PREPARATION OF DEOXYRIBONUCLEOSIDE PHOSPHORAMIDITES AND THEIR USE IN POLYMER-SUPPORTED SYNTHESIS OF OLIGODEOXYRIBONUCLEOTIDES
NIELSEN, J
TAAGAARD, M
MARUGG, JE
VANBOOM, JH
DAHL, O
[J]. NUCLEIC ACIDS RESEARCH, 1986, 14 (18) : 7391 - 7403
[8] PYRINDAMYCIN-A AND PYRINDAMYCIN-B, NEW ANTITUMOR ANTIBIOTICS
OHBA, K
WATABE, H
SASAKI, T
TAKEUCHI, Y
KODAMA, Y
NAKAZAWA, T
YAMAMOTO, H
SHOMURA, T
SEZAKI, M
KONDO, S
[J]. JOURNAL OF ANTIBIOTICS, 1988, 41 (10) : 1515 - 1519
[9] DUOCARMYCIN-A, A NEW ANTITUMOR ANTIBIOTIC FROM STREPTOMYCES
TAKAHASHI, I
TAKAHASHI, K
ICHIMURA, M
MORIMOTO, M
ASANO, K
KAWAMOTO, I
TOMITA, F
NAKANO, H
[J]. JOURNAL OF ANTIBIOTICS, 1988, 41 (12) : 1915 - 1917
[10] DNA-SEQUENCE SPECIFICITY OF MITOMYCIN CROSS-LINKING
TENG, SP
WOODSON, SA
CROTHERS, DM
[J]. BIOCHEMISTRY, 1989, 28 (09) : 3901 - 3907

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