EVIDENCE FOR EPOXIDASE ACTIVITY IN DEACETOXY DEACETYLCEPHALOSPORIN-C SYNTHASE

被引：7

作者：

BALDWIN, JE ^{[1
]}

ADLINGTON, RM ^{[1
]}

CROUCH, NP ^{[1
]}

PEREIRA, IAC ^{[1
]}

机构：

[1] UNIV OXFORD,OXFORD CTR MOLEC SCI,OXFORD OX1 3QY,ENGLAND

来源：

TETRAHEDRON | 1993年 / 49卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(01)80408-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conversion of the unnatural substrate exomethylene cephalosporin C by deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS) has been studied by the use of competitive kinetic isotope experiments. These suggest that the first irreversible event in this conversion does not involve C4-hydrogen abstraction. A novel epoxide cepham metabolite has been isolated from the enzymic conversion of [4-H-2]exomethylene cephalosporin C. It is believed that increased formation of this shunt metabolite is caused by the operation of a deuterium kinetic isotope effect on an enzyme-bound intermediate. The epoxide cepham is also accepted as a substrate by DAOC/DACS, being oxidised to an aldehyde product.

引用

页码：4907 / 4922

页数：16

共 25 条

[11] THE ENZYMATIC CONVERSION OF EXOMETHYLENE CEPHALOSPORIN-C INTO DEACETYL CEPHALOSPORIN-C AND THE ROLE OF MOLECULAR-OXYGEN IN CEPHALOSPORIN-C BIOSYNTHESIS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

CROUCH, NP ;

SCHOFIELD, CJ .

TETRAHEDRON, 1988, 44 (02) :643-650

[12] SUBSTRATE-SPECIFICITY OF SOLUBLE RECOMBINANT DEACETOXYCEPHALOSPORIN C/DEACETYLCEPHALOSPORIN C SYNTHASE [J].

BALDWIN, JE ;

ADLINGTON, RM ;

CROUCH, NP ;

HEATH, RJ ;

PEREIRA, IAC ;

SUTHERLAND, JD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (07) :669-672

[13]

BALDWIN JE, 1983, J CHEM SOC CHEM COMM, P153

[14]

CROUCH NP, 1988, THESIS OXFORD U

[15] NEW FINDINGS ON CEPHALOSPORIN-C BIOSYNTHESIS [J].

FUJISAWA, Y ;

SHIRAFUJI, H ;

KIDA, M ;

NARA, K ;

YONEDA, M ;

KANZAKI, T .

NATURE-NEW BIOLOGY, 1973, 246 (153) :154-155

[16]

GUTOWSKI GE, 1971, TETRAHEDRON LETT, V37, P3429

[17] POLAROGRAPHY OF CEPHALOSPORIN-C DERIVATIVES .1. 3-(5-METHYL-1,3,4-THIADIAZOL-2-YLTHIOMETHYL)-7-[2-(3-SYDNONE)-ACETAMIDO]-3-CEPHEM-4-CARBOXYLIC ACID, SODIUM SALT [J].

HALL, DA .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1973, 62 (06) :980-983

[18] ELECTROCHEMISTRY OF CEPHALOSPORIN-C DERIVATIVES .2. CEPHALOTHIN, SODIUM SALT [J].

HALL, DA ;

BERRY, DM ;

SCHNEIDER, CJ .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1977, 80 (01) :155-170

[19] PURIFICATION AND CHARACTERIZATION OF HYOSCYAMINE 6-BETA-HYDROXYLASE FROM ROOT CULTURES OF HYOSCYAMUS-NIGER L - HYDROXYLASE AND EPOXIDASE ACTIVITIES IN THE ENZYME PREPARATION [J].

HASHIMOTO, T ;

YAMADA, Y .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1987, 164 (02) :277-285

[20] STEADY-STATE ANALYSIS OF KINETIC ISOTOPE-EFFECTS IN ENZYMIC REACTIONS [J].

NORTHROP, DB .

BIOCHEMISTRY, 1975, 14 (12) :2644-2651

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