SYNTHESIS OF (2(R),3(S))[4-H-2(3)]VALINE - APPLICATION TO THE STUDY OF THE RING EXPANSION OF PENICILLIN-N BY DEACETOXYCEPHALOSPORIN-C SYNTHASE FROM STREPTOMYCES-CLAVULIGERUS

被引：9

作者：

BALDWIN, JE ^{[1
]}

ADLINGTON, RM ^{[1
]}

CROUCH, NP ^{[1
]}

MELLOR, LC ^{[1
]}

MORGAN, N ^{[1
]}

SMITH, AM ^{[1
]}

SUTHERLAND, JD ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1995年 / 51卷 / 14期

关键词：

D O I：

10.1016/0040-4020(95)00126-S

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of (<2(R)under bar>,<3(S)under bar>)[4-H-2(3)] valine was developed, and used to synthesise (<2(R)under bar>) [2'-H-2(3)]-penicillin N via a chemico-enzymatic synthesis. This labelled penicillin was then used to demonstrate the stereospecific ring expansion of penicillin N to deacetoxycephalosporin C by deacetoxycephalosporin C synthase from Streptomyces clavuligerus.

引用

页码：4089 / 4100

页数：12

共 25 条

[1] STUDIES ON BIOSYNTHESIS OF BETA-LACTAM ANTIBIOTICS .1. STEREOSPECIFIC SYNTHESES OF (2RS,3S)-[4,4,4-H-2(3)]-VALINE, (2RS,3S)-[4-H-3]-VALINE, (2RS,3R)-[4-H-3]-VALINE, AND (2RS,3S)-[4-C-13]-VALINE - INCORPORATION OF (2RS,3S)-[4-C-13]-VALINE INTO PENICILLIN-V [J].

ABERHART, DJ ;

LIN, LJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (20) :2320-2326

[2] A NEW METHOD FOR THE PREPARATION OF TERTIARY BUTYL ETHERS AND ESTERS [J].

ARMSTRONG, A ;

BRACKENRIDGE, I ;

JACKSON, RFW ;

KIRK, JM .

TETRAHEDRON LETTERS, 1988, 29 (20) :2483-2486

[3]

BAKER BJ, 1991, J BIOL CHEM, V266, P5087

[4] PENICILLIN BIOSYNTHESIS - ACTIVE-SITE MAPPING WITH AMINOADIPOYLCYSTEINYLVALINE VARIANTS [J].

BALDWIN, JE ;

ABRAHAM, EP ;

ADLINGTON, RM ;

BAHADUR, GA ;

CHAKRAVARTI, B ;

DOMAYNEHAYMAN, BP ;

FIELD, LD ;

FLITSCH, SL ;

JAYATILAKE, GS ;

SPAKOVSKIS, A ;

TING, HH ;

TURNER, NJ ;

WHITE, RL ;

USHER, JJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (18) :1225-1227

[5] HIGH-LEVEL SOLUBLE EXPRESSION OF ISOPENICILLIN-N SYNTHASE ISOZYMES IN ESCHERICHIA-COLI [J].

BALDWIN, JE ;

BLACKBURN, JM ;

SUTHERLAND, JD ;

WRIGHT, MC .

TETRAHEDRON, 1991, 47 (31) :5991-6002

[6] STEREOSPECIFIC SYNTHESIS OF DEALANYLALAHOPCIN [J].

BALDWIN, JE ;

ADLINGTON, RM ;

GOLLINS, DW ;

SCHOFIELD, CJ .

TETRAHEDRON, 1990, 46 (13-14) :4733-4748

[7] USE OF CHIRAL ISOPROPYL GROUPS IN BIOSYNTHESIS - SYNTHESIS OF (2RS,3S)-[4-C-13]VALINE [J].

BALDWIN, JE ;

LOLIGER, J ;

RASTETTER, W ;

NEUSS, N ;

HUCKSTEP, LL ;

DELAHIGU.N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (11) :3796-3797

[8] PURIFICATION AND INITIAL CHARACTERIZATION OF AN ENZYME WITH DEACETOXYCEPHALOSPORIN-C SYNTHETASE AND HYDROXYLASE-ACTIVITIES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

COATES, JB ;

CRABBE, MJC ;

CROUCH, NP ;

KEEPING, JW ;

KNIGHT, GC ;

SCHOFIELD, CJ ;

TING, HH ;

VALLEJO, CA ;

THORNILEY, M ;

ABRAHAM, EP .

BIOCHEMICAL JOURNAL, 1987, 245 (03) :831-841

[9] THE BIOSYNTHESIS OF PENICILLINS AND CEPHALOSPORINS [J].

BALDWIN, JE .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (01) :71-78

[10] CEPHALOSPORIN-C BIOSYNTHESIS - STEREOCHEMISTRY OF THE INCORPORATION OF D,L,D-ALPHA-AMINODIPOYL-CYSTEINYL-(3S)-[2-2H,4-C-13]VALINE INTO BETA-LACTAM COMPOUNDS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

CROUCH, NP ;

TURNER, NJ ;

SCHOFIELD, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (16) :1141-1143

← 1 2 3 →