AVERMECTIN BIOSYSTHESIS - INTACT INCORPORATION OF A DIKETIDE CHAIN-ASSEMBLY INTERMEDIATE INTO THE POLYKETIDE MACROCYCLIC RING

被引：16

作者：

DUTTON, CJ

HOOPER, AM

LEADLAY, PF

STAUNTON, J

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND

[2] PFIZER LTD,CENT RES DIV,SANDWICH CT13 9NJ,KENT,ENGLAND

[3] DEPT BIOCHEM,CAMBRIDGE CB2 1QW,ENGLAND

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(00)76544-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Incorporation experiments in Streptomyces avermitilis with synthetic analogues of the proposed diketide intermediate support the processive mechanism of chain assembly in the biosynthesis of the polyketide core of the avermectin structure. Specific incorporation of a C-13 labelled precursor was established by C-13 NMR; intact incorporation of two deuterium-labelled analogues was established by electrospray mass spectrometry (ESMS).

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页码：327 / 330

页数：4

相关论文

共 12 条

[1] AVERMECTINS, NEW FAMILY OF POTENT ANTHELMINTIC AGENTS - PRODUCING ORGANISM AND FERMENTATION [J].

BURG, RW ;

MILLER, BM ;

BAKER, EE ;

BIRNBAUM, J ;

CURRIE, SA ;

HARTMAN, R ;

KONG, YL ;

MONAGHAN, RL ;

OLSON, G ;

PUTTER, I ;

TUNAC, JB ;

WALLICK, H ;

STAPLEY, EO ;

OIWA, R ;

OMURA, S .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 15 (03) :361-367

[2] MACROLIDE BIOSYNTHESIS .4. INTACT INCORPORATION OF A CHAIN-ELONGATION INTERMEDIATE INTO ERYTHROMYCIN [J].

CANE, DE ;

YANG, CC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1255-1257

[3] BIOSYNTHETIC ORIGIN OF THE CARBON SKELETON AND OXYGEN-ATOMS OF THE AVERMECTINS [J].

CANE, DE ;

LIANG, TC ;

KAPLAN, L ;

NALLIN, MK ;

SCHULMAN, MD ;

HENSENS, OD ;

DOUGLAS, AW ;

ALBERSSCHONBERG, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4110-4112

[4] LL-F28249 ANTIBIOTIC COMPLEX - A NEW FAMILY OF ANTIPARASITIC MACROCYCLIC LACTONES - ISOLATION, CHARACTERIZATION AND STRUCTURES OF LL-F28249 ALPHA-BETA-GAMMA-LAMBDA [J].

CARTER, GT ;

NIETSCHE, JA ;

HERTZ, MR ;

WILLIAMS, DR ;

SIEGEL, MM ;

MORTON, GO ;

JAMES, JC ;

BORDERS, DB .

JOURNAL OF ANTIBIOTICS, 1988, 41 (04) :519-529

[5] FURTHER-STUDIES ON THE BIOSYNTHESIS OF THE AVERMECTINS [J].

CHEN, TS ;

ARISON, BH ;

GULLO, VP ;

INAMINE, ES .

JOURNAL OF INDUSTRIAL MICROBIOLOGY, 1989, 4 (03) :231-237

[6] NOVEL AVERMECTINS PRODUCED BY MUTATIONAL BIOSYNTHESIS [J].

DUTTON, CJ ;

GIBSON, SP ;

GOUDIE, AC ;

HOLDOM, KS ;

PACEY, MS ;

RUDDOCK, JC ;

BULOCK, JD ;

RICHARDS, MK .

JOURNAL OF ANTIBIOTICS, 1991, 44 (03) :357-365

[7] BRANCHED-CHAIN FATTY-ACID REQUIREMENT FOR AVERMECTIN PRODUCTION BY A MUTANT OF STREPTOMYCES-AVERMITILIS LACKING BRANCHED-CHAIN 2-OXO ACID DEHYDROGENASE-ACTIVITY [J].

HAFNER, EW ;

HOLLEY, BW ;

HOLDOM, KS ;

LEE, SE ;

WAX, RG ;

BECK, D ;

MCARTHUR, HAI ;

WERNAU, WC .

JOURNAL OF ANTIBIOTICS, 1991, 44 (03) :349-356

[8] ACYCLIC STEREOSELECTION .13. ARYL ESTERS - REAGENTS FOR THREO-ALDOLIZATION [J].

HEATHCOCK, CH ;

PIRRUNG, MC ;

MONTGOMERY, SH ;

LAMPE, J .

TETRAHEDRON, 1981, 37 (23) :4087-4095

[9]

HUTCHINSON CR, 1987, J AM CHEM SOC, V109, P1253

[10] COMPLEX ORGANIZATION OF THE STREPTOMYCES-AVERMITILIS GENES ENCODING THE AVERMECTIN POLYKETIDE SYNTHASE [J].

MACNEIL, DJ ;

OCCI, JL ;

GEWAIN, KM ;

MACNEIL, T ;

GIBBONS, PH ;

RUBY, CL ;

DANIS, SJ .

GENE, 1992, 115 (1-2) :119-125