BIOSYNTHETIC-STUDIES ON THE CHITINASE INHIBITOR, ALLOSAMIDIN - ORIGIN OF THE CARBON AND NITROGEN-ATOMS

被引：28

作者：

ZHOU, ZY ^{[1
]}

SAKUDA, S ^{[1
]}

YAMADA, Y ^{[1
]}

机构：

[1] OSAKA UNIV,FAC ENGN,DEPT BIOTECHNOL,YAMADA-OKA 2-1,SUITA,OSAKA 565,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 13期

关键词：

D O I：

10.1039/p19920001649

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allosamidin 1 is a potent insect chitinase inhibitor produced by Streptomyces sp. The biosynthesis of compound 1 was studied by feeding experiments with labelled precursors. Incorporation experiments using [1-C-13]- and D-[6-C-13]glucose as well as doubly labelled D-[1-C-13,2-N-15]-glucosamine revealed that each skeleton of N-acetyl-D-allosamine and allosamizoline 2 was derived froM D-glucosamine. Further experiments with L-[guanidino-C-13,N-15(2)]arginine and [methyl-C-13]-methionine clarified the origin of the dimethylaminooxazoline moiety of compound 2.

引用

页码：1649 / 1652

页数：4

共 25 条

[1] KLUYVEROMYCES-LACTIS TOXIN HAS AN ESSENTIAL CHITINASE ACTIVITY [J].

BUTLER, AR ;

ODONNELL, RW ;

MARTIN, VJ ;

GOODAY, GW ;

STARK, MJR .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1991, 199 (02) :483-488

[2]

CAPRIOLI RM, 1972, BIOCH APPLICATIONS M, P735

[3]

DICKINSON K, 1989, J GEN MICROBIOL, V135, P1417

[4] PROKARYOTIC HOPANOIDS - THE BIOSYNTHESIS OF THE BACTERIOHOPANE SKELETON - FORMATION OF ISOPRENIC UNITS FROM 2 DISTINCT ACETATE POOLS AND A NOVEL TYPE OF CARBON CARBON LINKAGE BETWEEN A TRITERPENE AND D-RIBOSE [J].

FLESCH, G ;

ROHMER, M .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1988, 175 (02) :405-411

[5] CHITINASE IN FEMALE ONCHOCERCA-GIBSONI AND ITS INHIBITION BY ALLOSAMIDIN [J].

GOODAY, GW ;

BRYDON, LJ ;

CHAPPELL, LH .

MOLECULAR AND BIOCHEMICAL PARASITOLOGY, 1988, 29 (2-3) :223-225

[6] TOTAL SYNTHESIS OF ALLOSAMIDIN - AN APPLICATION OF THE SULFONAMIDOGLYCOSYLATION OF GLYCALS [J].

GRIFFITH, DA ;

DANISHEFSKY, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5863-5864

[7] BIOSYNTHESIS OF INDOLMYCIN [J].

HORNEMANN, U ;

HURLEY, LH ;

SPEEDIE, MK ;

FLOSS, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :3028-+

[8] STRUCTURE OF DEMETHYLALLOSAMIDIN AS AN INSECT CHITINASE INHIBITOR [J].

ISOGAI, A ;

SATO, M ;

SAKUDA, S ;

NAKAYAMA, J ;

SUZUKI, A .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1989, 53 (10) :2825-2826

[9] SPECIFIC-INHIBITION OF BOMBYX-MORI CHITINASE BY ALLOSAMIDIN [J].

KOGA, D ;

ISOGAI, A ;

SAKUDA, S ;

MATSUMOTO, S ;

SUZUKI, A ;

KIMURA, S ;

IDE, A .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1987, 51 (02) :471-476

[10]

LEVY GC, 1979, NITROGEN 15 NUCLEAR

← 1 2 3 →