Solid-phase synthesis and biological activity of malformin C and its derivatives

被引：20

作者：

Kojima, Yasuhiro ^{[2
]}

Sunazuka, Toshiaki ^{[1
,2
]}

Nagai, Kenichiro ^{[2
]}

Hirose, Tomoyasu ^{[2
]}

Namatame, Miyuki ^{[3
]}

Ishiyama, Aki ^{[3
]}

Otoguro, Kazuhiko ^{[3
]}

Omura, Satoshi ^{[2
]}

机构：

[1] Kitasato Univ, Kitasato Inst Life Sci, Kitasato Inst, Minato Ku, Tokyo 1088641, Japan

[2] Kitasato Univ, Grad Sch Infect Control Sci, Tokyo 1088641, Japan

[3] Kitasato Univ, Kitasato Inst Life Sci, Res Ctr Trop Dis, Tokyo 1088641, Japan

来源：

JOURNAL OF ANTIBIOTICS | 2009年 / 62卷 / 12期

关键词：

antimalarial activity; antitrypanosomal activity; cyclic pentapeptide; disulfide bond; malformins; solid-phase synthesis; ASPERGILLUS-NIGER; METABOLITE; CURVATURES; PEPTIDES; CELLS;

D O I：

10.1038/ja.2009.100

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

We accomplished the solid-phase total synthesis of malformin C, which is adaptable for the easy preparation of various derivatives. A solid-phase total synthesis of malformin C was achieved by on-resin macrolactannization and disulfide bond formation, with concurrent cleavage from the resin. Antimalarial and antitrypanosomal activities were examined, which helped elucidate partial structure-activity relationships. Results indicate that the disulfide bond is essential and branched amino acids are also crucial components if the compound is to exhibit potent antimalarial and antitrypanosomal properties. The Journal of Antibiotics (2009) 62, 681-686; doi:10.1038/ja.2009.100; published online 30 October 2009

引用

页码：681 / 686

页数：6

共 30 条

[1] MALFORMIN-C, A NEW METABOLITE OF ASPERGILLUS-NIGER [J].

ANDEREGG, RJ ;

BIEMANN, K ;

BUCHI, G ;

CUSHMAN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (11) :3365-3370

[2]

[Anonymous], WORLD MAL REP 2008

[3]

ANZAI KENTARO, 1965, PHYTOCHEMISTRY, V4, P713, DOI 10.1016/S0031-9422(00)86240-8

[4]

ANZAI KENTARO, 1965, PHYTOCHEMISTRY, V4, P263, DOI 10.1016/S0031-9422(00)86172-5

[5] STRUCTURE AND SYNTHESIS OF MALFORMIN-A [J].

BODANSZK.M ;

STAHL, GL .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1974, 71 (07) :2791-2794

[6] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ENANTIO-[5-VALINE]MALFORMIN, A PALINDROME PEPTIDE [J].

BODANSZKY, M ;

STAHL, GL ;

CURTIS, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (10) :2857-2859

[7] CURVATURES AND MALFORMATIONS IN BEAN PLANTS CAUSED BY CULTURE FILTRATE OF ASPERGILLUS NIGER [J].

CURTIS, RW .

PLANT PHYSIOLOGY, 1958, 33 (01) :17-22

[8] ROOT CURVATURES INDUCED BY CULTURE FILTRATES OF ASPERGILLUS NIGER [J].

CURTIS, RW .

SCIENCE, 1958, 128 (3325) :661-662

[9] STUDIES ON RESPONSE OF BEAN SEEDLINGS AND CORN ROOTS TO MALFORMIN [J].

CURTIS, RW .

PLANT PHYSIOLOGY, 1961, 36 (01) :37-&

[10] MYCOTOXINS FROM MOLD FUNGI - WEAPONS OF UNINIVITED FELLOW-BOARDERS OF MAN AND ANIMAL - STRUCTURES, BIOLOGICAL-ACTIVITY, BIOSYNTHESIS, AND PRECAUTIONS [J].

FRANCK, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1984, 23 (07) :493-505

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