Utahmycins A and B, Azaquinones Produced by an Environmental DNA Clone

被引：46
作者：
Bauer, John D. [1 ]
King, Ryan W. [1 ]
Brady, Sean F. [1 ]
机构：
[1] Rockefeller Univ, Howard Hughes Med Inst, Lab Genetically Encoded Small Mol, New York, NY 10065 USA
来源：
JOURNAL OF NATURAL PRODUCTS | 2010年 / 73卷 / 05期
关键词：
NAPHTHOQUINONE PIGMENTS; AZAANTHRAQUINONE; BIOSYNTHESIS; FUSARIUM; FUNGUS; DIHYDROFUSARUBIN; POLYKETIDES; METABOLITES; SCORPINONE; PATHWAY;
D O I：
10.1021/np900786s
中图分类号：
Q94 [植物学];
学科分类号：
071001 ;
摘要：
Two new azaquinones, utahmycins A (1) and B (2), were isolated from cultures of Streptomyces albus J1704 transformed with the environmental DNA-derived Erd gene cluster. The structures of 1 and 2 were elucidated by spectroscopic analyses. The structure of 1 was confirmed by single-crystal X-ray diffraction analysis. Both metabolites appear to arise from the addition of a nitrogen atom to erdacin biosynthetic intermediates. Utahmycin A (1) is the first example of a biologically derived 1,3-dimethyl-2-azaanthraquinone.
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收藏
页码：976 / 979
页数：4
相关论文
共 28 条
[1]  
[Anonymous], 1990, Biol Metals
[2]  
ARSENAULT G. P., 1965, TETRAHED RON LETT, V45, P4033
[3]   ANTIMICROBIAL ACTIVITY OF NAPHTHOQUINONES FROM FUSARIA [J].
BAKER, RA ;
TATUM, JH ;
NEMEC, S .
MYCOPATHOLOGIA, 1990, 111 (01) :9-15
[4]   Cloning and characterization of new glycopeptide gene clusters found in an environmental DNA megalibrary [J].
Banik, Jacob J. ;
Brady, Sean F. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2008, 105 (45) :17273-17277
[5]   Construction of soil environmental DNA cosmid libraries and screening for clones that produce biologically active small molecules [J].
Brady, Sean F. .
NATURE PROTOCOLS, 2007, 2 (05) :1297-1305
[6]  
GRAFE U, 1991, PHARMAZIE, V46, P297
[7]  
HAMILTON MA, 1953, ANTIBIOT CHEMOTHER, V3, P853
[8]  
KHANAPURE SP, 1988, HETEROCYCLES, V27, P2643
[9]   An Environmental DNA-Derived Type II Polyketide Biosynthetic Pathway Encodes the Biosynthesis of the Pentacyclic Polyketide Erdacin [J].
King, Ryan W. ;
Bauer, John D. ;
Brady, Sean F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (34) :6257-6261
[10]   Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds [J].
Koyama, J ;
Morita, I ;
Kobayashi, N ;
Osakai, T ;
Usuki, Y ;
Taniguchi, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (04) :1079-1082
123