Erythronolides H and I, New Erythromycin Congeners from a New Halophilic Actinomycete Actinopolyspora sp YIM90600

被引：28

作者：

Huang, Sheng-Xiong ^{[1
,2
]}

Zhao, Li-Xing ^{[1
,3
]}

Tang, Shu-Kun ^{[3
]}

Jiang, Cheng-Lin ^{[3
]}

Duan, Yanwen

Shen, Ben ^{[1
,4
,5
]}

机构：

[1] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA

[2] Hunan Engn Res Ctr Combinatorial Biosynth & Nat P, Changsha 410329, Hunan, Peoples R China

[3] Yunnan Univ, Yunnan Inst Microbiol, Kunming 650091, Yunnan, Peoples R China

[4] Univ Wisconsin, Natl Cooperat Drug Discovery Grp, Madison, WI 53705 USA

[5] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 06期

关键词：

STREPTOMYCES-VENEZUELAE; POLYKETIDE SYNTHASE; SP-NOV; BIOSYNTHESIS; DERIVATIVES; RESISTANT; CYTOCHROME-P450; MACROLACTONES; NARBOMYCIN; KETOLIDES;

D O I：

10.1021/ol900143j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Erythronolides H and I, novel congeners of the clinically important antibacterial drug erythromycin A, have been isolated from the new halophilic actinomycete Actinopolyspora sp. YIM90600. In addition to producing the new erythromycin congeners, A. sp. YIM90600 produces erythromycin C in a high titer. The presence of the C-14 hydroxyl moiety and the C-6/C-18-epoxide in erythronolide H and the spiroketal moiety of erythronolide I sheds new insights into structural diversity of erythromycin analog libraries potentially accessible by combinatorial biosynthesis.

引用

页码：1353 / 1356

页数：4

共 36 条

[1]

ADACHI TS, 1988, ANTIBIOT, V41, P966

[2] Characterization of the macrolide P-450 hydroxylase from Streptomyces venezuelae which converts narbomycin to picromycin [J].

Betlach, MC ;

Kealey, JT ;

Betlach, MC ;

Ashley, GW ;

McDaniel, R .

BIOCHEMISTRY, 1998, 37 (42) :14937-14942

[3] SYNTHESIS, INVITRO AND INVIVO ACTIVITY OF NOVEL 9-DEOXO-9A-AZA-9A-HOMOERYTHROMYCIN A DERIVATIVES - A NEW CLASS OF MACROLIDE ANTIBIOTICS, THE AZALIDES [J].

BRIGHT, GM ;

NAGEL, AA ;

BORDNER, J ;

DESAI, KA ;

DIBRINO, JN ;

NOWAKOWSKA, J ;

VINCENT, L ;

WATROUS, RM ;

SCIAVOLINO, FC ;

ENGLISH, AR ;

RETSEMA, JA ;

ANDERSON, MR ;

BRENNAN, LA ;

BOROVOY, RJ ;

CIMOCHOWSKI, CR ;

FAIELLA, JA ;

GIRARD, AE ;

GIRARD, D ;

HERBERT, C ;

MANOUSOS, M ;

MASON, R .

JOURNAL OF ANTIBIOTICS, 1988, 41 (08) :1029-1047

[4] Preparation of clarithromycin.: Selective 6-O-methylation of the novel erythromycin A 9-O-(2-pyrimidyl)oxime [J].

Brunet, Ernesto ;

Munoz, Dulce Maria ;

Parra, Francisco ;

Mantecon, Susana ;

Juanes, Olga ;

Rodriguez-Ubis, Juan Carlos ;

Cruzado, Ma Carmen ;

Asensio, Ramon .

TETRAHEDRON LETTERS, 2007, 48 (08) :1321-1324

[5] Methymycin biosynthesis.: Isolation of P450 monooxygenase activity in a cell-free system from Streptomyces venezuelae [J].

Cane, DE ;

Graziani, EI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2682-2683

[6]

CORTES J, 1995, SCIENCE, V268, P1497

[7] Activity of the novel macrolide BAL19403 against ribosomes from erythromycin-resistant Propionibacterium acnes [J].

Dreier, Jurg ;

Amantea, Eva ;

Kellenberger, Laurenz ;

Page, Malcolm G. P. .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2007, 51 (12) :4361-4365

[8] Parallel pathways for oxidation of 14-membered polyketide macrolactones in Saccharopolyspora erythraea [J].

Gaisser, S ;

Lill, R ;

Staunton, J ;

Méndez, C ;

Salas, J ;

Leadlay, PF .

MOLECULAR MICROBIOLOGY, 2002, 44 (03) :771-781

[9] NEW ETHER OXIME DERIVATIVES OF ERYTHROMYCIN-A - A STRUCTURE-ACTIVITY RELATIONSHIP STUDY [J].

GASC, JC ;

DAMBRIERES, SG ;

LUTZ, A ;

CHANTOT, JF .

JOURNAL OF ANTIBIOTICS, 1991, 44 (03) :313-330

[10] ISOLATION AND CHARACTERIZATION OF ACTINOPOLYSPORA-HALOPHILA, GEN ET SP-NOV, AN EXTREMELY HALOPHILIC ACTINOMYCETE [J].

GOCHNAUER, MB ;

LEPPARD, GG ;

KOMARATAT, P ;

KATES, M ;

NOVITSKY, T ;

KUSHNER, DJ .

CANADIAN JOURNAL OF MICROBIOLOGY, 1975, 21 (10) :1500-1511

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