PHOTOGENERATION OF HIGHLY ELECTROPHILIC BENZOYLKETENE FROM DIBENZOYLDIAZOMETHANE IN AQUEOUS SOLVENTS - REACTION WITH AMINO-ACIDS AND DNA CLEAVAGE

被引：16

作者：

NAKATANI, K

SHIRAI, J

TAMAKI, R

SAITO, I

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT SYNTHET CHEM & BIOL CHEM,KYOTO 60601,JAPAN

[2] JRDC,PRESTO,KYOTO 60601,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 30期

关键词：

D O I：

10.1016/0040-4039(95)01040-O

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photoirradiation of dibenzoyldiazomethane in the presence of amino acid derivatives in aqueous solutions efficiently produced the addition products through a reaction with photogenerated benzoylketene. Efficient DNA cleavage was observed with a dibenzoyldiazomethane derivative, possessing a cationic side chain under photoirradiation conditions.

引用

收藏

页码：5363 / 5366

页数：4

相关论文

共 10 条

[1] PHOTOCHEMISTRY OF DIAZODIBENZOYLMETHANE - PHOTOREACTION DEPENDENT ON WAVE LENGTH AND TEMPERATURE [J].

BAUMANN, N .

HELVETICA CHIMICA ACTA, 1972, 55 (08) :2716-&

[2]

Gill G.B., 1991, COMPREHENSIVE ORGANI, V3, P887

[3] PHOTOCHEMISTRY OF QUINOLYLMETHYLISOTHIORONIUM SALTS - GUANINE SELECTIVE DNA PHOTOCLEAVAGE REAGENTS [J].

HENRIKSEN, U ;

LARSEN, C ;

KARUP, G ;

JEPPESEN, C ;

NIELSEN, PE ;

BUCHARDT, O .

PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1991, 53 (03) :299-305

[4] N-METHOXYDIACETAMIDE - A NEW SELECTIVE ACETYLATING AGENT [J].

KIKUGAWA, Y ;

MITSUI, K ;

SAKAMOTO, T .

TETRAHEDRON LETTERS, 1990, 31 (02) :243-246

[5] BETA-KETO CARBOXYLIC-ACIDS STABILIZED BY STERIC EFFECTS [J].

MEIER, H ;

WENGENROTH, H ;

LAUER, W ;

KRAUSE, V .

TETRAHEDRON LETTERS, 1989, 30 (39) :5253-5256

[6] WOLFF REARRANGEMENT OF ALPHA-DIAZO CARBONYL-COMPOUNDS [J].

MEIER, H ;

ZELLER, KP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (01) :32-43

[7] PHOTOINDUCED DNA CLEAVAGE BY DESIGNED MOLECULES WITH CONJUGATED ENE-YNE-KETENE FUNCTIONALITIES [J].

NAKATANI, K ;

ISOE, S ;

MAEKAWA, S ;

SAITO, I .

TETRAHEDRON LETTERS, 1994, 35 (04) :605-608

[8] ADENOSINE-GUANOSINE PREFERENTIAL PHOTOCLEAVAGE OF DNA BY AZIDO-BENZOYLPENTADIENYLCARBONYLOXY AND DIAZOCYCLOPENTADIENYLCARBONYLOXY DERIVATIVES OF 9-AMINOACRIDINE [J].

NIELSEN, PE ;

JEPPESEN, C ;

EGHOLM, M ;

BUCHARDT, O .

NUCLEIC ACIDS RESEARCH, 1988, 16 (09) :3877-3889

[9] PHOTOGENERATION OF CARBOCATION VIA INTRAMOLECULAR ELECTRON-TRANSFER - PHOTOINDUCED DNA ALKYLATION [J].

SAITO, I ;

TAKAYAMA, M ;

SAKURAI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2653-2654

[10] MECHANISM OF THE PHOTOCHEMICAL AND THERMAL WOLFF REARRANGEMENT OF 2-DIAZO-1,3-DICARBONYL COMPOUNDS [J].

TOMIOKA, H ;

HAYASHI, N ;

ASANO, T ;

IZAWA, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (03) :758-761