ON THE ORIGIN OF PHOTO-LABILITY OF NEOCARZINOSTATIN CHROMOPHORE

被引：12

作者：

GOMIBUCHI, T ^{[1
]}

FUJIWARA, K ^{[1
]}

NEHIRA, T ^{[1
]}

HIRAMA, M ^{[1
]}

机构：

[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)73852-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Central pathway of photochemical decomposition of the 10-membered ring analog 9 proved to be a fragmentation reaction of naphthoate ester, an analog to Norrish Type II split, leading to the formation of unstable fulvene derivative 10 and 2-hydroxy-7-methoxy-5-methyl-1-naphthoic acid 4, which implied the mechanism of photodecomposition of neocarzinostatin chromophore 1.

引用

页码：5753 / 5756

页数：4

共 14 条

[1]

CALVERT JG, 1966, PHOTOCHEMISTRY, P434

[2] AN ANTITUMOR POLYPEPTIDE ANTIBIOTIC NEOCARZINOSTATIN - THE MODE OF APOPROTEIN - CHROMOPHORE INTERACTION [J].

EDO, K ;

SAITO, K ;

AKIYAMAMURAI, Y ;

MIZUGAKI, M ;

KOIDE, Y ;

ISHIDA, N .

JOURNAL OF ANTIBIOTICS, 1988, 41 (04) :554-562

[3] THE STRUCTURE OF NEOCARZINOSTATIN CHROMOPHORE POSSESSING A NOVEL BICYCLO-[7,3,0]DODECADIYNE SYSTEM [J].

EDO, K ;

MIZUGAKI, M ;

KOIDE, Y ;

SETO, H ;

FURIHATA, K ;

OTAKE, N ;

ISHIDA, N .

TETRAHEDRON LETTERS, 1985, 26 (03) :331-334

[4] MECHANISM OF NEOCARZINOSTATIN ACTION - ROLE OF DNA MICROSTRUCTURE IN DETERMINATION OF CHEMISTRY OF BISTRANDED OXIDATIVE DAMAGE [J].

GOLDBERG, IH .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (07) :191-198

[5] SYNTHESIS AND DNA-CLEAVING ABILITIES OF FUNCTIONAL NEOCARZINOSTATIN CHROMOPHORE ANALOGS - BASE DISCRIMINATION BY A SIMPLE ALCOHOL [J].

HIRAMA, M ;

GOMIBUCHI, T ;

FUJIWARA, K ;

SUGIURA, Y ;

UESUGI, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9851-9853

[6]

ISHIDA N, 1965, J ANTIBIOT, V18, P68

[7] STEREOCHEMICAL ASSIGNMENT OF NEOCARZINOSTATIN CHROMOPHORE - STRUCTURES OF NEOCARZINOSTATIN CHROMOPHORE METHYL THIOGLYCOLATE ADDUCTS [J].

MYERS, AG ;

PROTEAU, PJ ;

HANDEL, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (21) :7212-7214

[8] EFFECT OF NON-PROTEIN CHROMOPHORE REMOVAL ON NEOCARZINOSTATIN ACTION [J].

NAPIER, MA ;

KAPPEN, LS ;

GOLDBERG, IH .

BIOCHEMISTRY, 1980, 19 (09) :1767-1773

[9]

NAPIER MA, 1983, MOL PHARMACOL, V23, P500

[10] A SIMPLE AND EFFICIENT SYNTHESIS OF THE NAPHTHOATE MOIETY OF NEOCARZINOSTATIN CHROMOPHORE [J].

TAKAHASHI, K ;

SUZUKI, T ;

HIRAMA, M .

TETRAHEDRON LETTERS, 1992, 33 (32) :4603-4604

← 1 2 →