OXIDATION OF ALKENES BY A CHIRAL NON-PORPHYRINIC OXIDIZING CATALYST BASED ON THE BLEOMYCIN-FE(II) COMPLEX

被引：38

作者：

SUGA, A

SUGIYAMA, T

OTSUKA, M

OHNO, M

SUGIURA, Y

MAEDA, K

机构：

[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN

[2] INST MICROBIAL CHEM,SHINAGAWA KU,TOKYO 141,JAPAN

[3] KYOTO UNIV,INST CHEM RES,UJI,KYOTO 611,JAPAN

来源：

TETRAHEDRON | 1991年 / 47卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(01)86376-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic model for the metal binding site of bleomycin with 4-dimethylaminopyridine nucleus, namely PYML-8, shows dioxygen activation up to 125% of that of bleomycin. beta-Methylstyrene is oxidated with the Fe(III)-H2O2, Fe(III)-PhIO, or Fe(II)-O2 complex systems of PYML-8 to give a set of products including optically active epoxide. The product composition is dependent on iron, oxygen source, and reducing agent employed, suggesting varied active species generated from each complex system.

引用

收藏

页码：1191 / 1204

页数：14

相关论文

共 31 条

[11] SYNTHETIC STUDIES ON AN ANTITUMOR ANTIBIOTIC, BLEOMYCIN .26. CHIRAL ENVIRONMENT AROUND THE METAL CENTER OBSERVED BY THE EPOXIDATION WITH THE IRON COMPLEXES OF BLEOMYCIN AND THE SYNTHETIC ANALOG [J].

KAKU, Y ;

OTSUKA, M ;

OHNO, M .

CHEMISTRY LETTERS, 1989, (04) :611-614

[12]

KITTAKA A, 1988, TETRAHEDRON, V44, P2811

[13] TRANSITION-METAL BINDING-SITE OF BLEOMYCIN - A REMARKABLY EFFICIENT DIOXYGEN-ACTIVATING MOLECULE BASED ON BLEOMYCIN-FE(II) COMPLEX [J].

KITTAKA, A ;

SUGANO, Y ;

OTSUKA, M ;

OHNO, M ;

SUGIURA, Y ;

UMEZAWA, H .

TETRAHEDRON LETTERS, 1986, 27 (31) :3631-3634

[14] MAN-DESIGNED BLEOMYCINS - SYNTHESIS OF DIOXYGEN ACTIVATING MOLECULES AND A DNA CLEAVING MOLECULE BASED ON BLEOMYCIN-FE(II)-O2 COMPLEX [J].

KITTAKA, A ;

SUGANO, Y ;

OTSUKA, M ;

OHNO, M .

TETRAHEDRON, 1988, 44 (10) :2821-2833

[15] DIRECT COMPARISON OF OXYGEN-TRANSFER BY IRON BLEOMYCIN AND ZINC BLEOMYCIN [J].

LONG, EC ;

HECHT, SM .

TETRAHEDRON LETTERS, 1988, 29 (49) :6413-6416

[16] POSSIBLE ROLE OF LEWIS ACID CATALYSIS IN THE OXIDATION OF ALKENES AND ALPHA,BETA-UNSATURATED KETONES USING BLEOMYCIN-ZN(II) AND BLEOMYCIN-FE(III)-IODOSYLBENZENE IN AQUEOUS METHANOL [J].

MORIARTY, RM ;

PENMASTA, R ;

PRAKASH, I .

TETRAHEDRON LETTERS, 1985, 26 (39) :4699-4702

[17]

MURUGESAN N, 1982, J BIOL CHEM, V257, P8600

[18] BLEOMYCIN AS AN OXENE TRANSFERASE - CATALYTIC OXYGEN-TRANSFER TO OLEFINS [J].

MURUGESAN, N ;

HECHT, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (02) :493-500

[19] NEW AGENTS FOR TERTIARY BUTYLOXYCARBONYLATION AND PARA METHOXYBENZYL-OXYCARBONYLATION OF AMINO-ACIDS [J].

NAGASAWA, T ;

KUROIWA, K ;

NARITA, K ;

ISOWA, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (04) :1269-1272

[20]

OHNO M, 1988, International Journal of Experimental and Clinical Chemotherapy, V1, P12

← 1 2 3 4 →