Nitropyrrole natural products: isolation, biosynthesis and total synthesis

被引:25
作者
Ding, Xiao-Bo [1 ]
Brimble, Margaret A. [1 ,2 ]
Furkert, Daniel P. [1 ,2 ]
机构
[1] Univ Auckland, Sch Chem Sci, 23 Symonds St, Auckland 1010, New Zealand
[2] Univ Auckland, Maurice Wilkins Ctr Mol Biodiscovery, Private Bag 92019, Auckland 1010, New Zealand
关键词
PYRROLOMYCIN-B; N-OXYGENASE; STREPTOMYCES-FUMANUS; HERONAPYRROLE C; NITRO-COMPOUNDS; DIOXAPYRROLOMYCIN; ANTIBIOTICS; ENHANCEMENT; REDUCTION; NITRATION;
D O I
10.1039/c5ob02599k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitropyrrole-containing natural products are relatively rare in nature. Known examples are limited to the beta-nitropyrrole-containing pyrrolomycins and a-nitropyrrole-containing nitropyrrolins and heronapyrroles. Their unique structures and interesting bioactivity are of ongoing interest to the chemistry community. This review describes the isolation, biological activity, biosynthesis and chemical synthesis of nitropyrrolecontaining natural products reported to date.
引用
收藏
页码:5390 / 5401
页数:12
相关论文
共 36 条
[1]  
BUDESINSKY Z, 1975, COLLECT CZECH CHEM C, V40, P1078
[2]   DIRECT BIOCHEMICAL NITRATION IN THE BIOSYNTHESIS OF DIOXAPYRROLOMYCIN - A UNIQUE MECHANISM FOR THE INTRODUCTION OF NITRO-GROUPS IN MICROBIAL PRODUCTS [J].
CARTER, GT ;
NIETSCHE, JA ;
GOODMAN, JJ ;
TORREY, MJ ;
DUNNE, TS ;
SIEGEL, MM ;
BORDERS, DB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (17) :1271-1273
[3]   Dioxapyrrolomycin biosynthesis in Streptomyces fumanus [J].
Charan, RD ;
Schlingmann, G ;
Bernan, VS ;
Feng, XD ;
Carter, GT .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (01) :29-33
[4]   Additional pyrrolomycins from cultures of Streptomyces fumanus [J].
Charan, RD ;
Schlingmann, G ;
Bernan, VS ;
Feng, XD ;
Carter, GT .
JOURNAL OF NATURAL PRODUCTS, 2005, 68 (02) :277-279
[5]   ANTHELMINTIC ACTIVITY OF DIOXAPYRROLOMYCIN [J].
CONDER, GA ;
ZIELINSKI, RJ ;
JOHNSON, SS ;
KUO, MST ;
COX, DL ;
MARSHALL, VP ;
HABER, CL ;
DIROMA, PJ ;
NELSON, SJ ;
CONKLIN, RD ;
LEE, BL ;
GEARY, TG ;
ROTHWELL, JT ;
SANGSTER, NC .
JOURNAL OF ANTIBIOTICS, 1992, 45 (06) :977-983
[6]   A MECHANISTICALLY DESIGNED BIS-CINCHONA ALKALOID LIGAND ALLOWS POSITION-SELECTIVE AND ENANTIOSELECTIVE DIHYDROXYLATION OF FARNESOL AND OTHER OLIGOPRENYL DERIVATIVES AT THE TERMINAL ISOPROPYLIDENE UNIT [J].
COREY, EJ ;
NOE, MC ;
LIN, SZ .
TETRAHEDRON LETTERS, 1995, 36 (48) :8741-8744
[7]   Total Synthesis of Heronapyrrole C [J].
Ding, Xiao-Bo ;
Furkert, Daniel P. ;
Capon, Robert J. ;
Brimble, Margaret A. .
ORGANIC LETTERS, 2014, 16 (02) :378-381
[8]  
EDWARDS DI, 1990, NATO ADV SCI I A-LIF, V198, P275
[9]   NEW CHLORINATED NITRO-PYRROLE ANTIBIOTICS, PYRROLOMYCIN-A AND PYRROLOMYCIN-B (SF-2080-A AND SF-2080-B) [J].
EZAKI, N ;
SHOMURA, T ;
KOYAMA, M ;
NIWA, T ;
KOJIMA, M ;
INOUYE, S ;
ITO, T ;
NIIDA, T .
JOURNAL OF ANTIBIOTICS, 1981, 34 (10) :1363-1365
[10]   PYRROLOMYCIN-C, PYRROLOMYCIN-D AND PYRROLOMYCIN-E, NEW MEMBERS OF PYRROLOMYCINS [J].
EZAKI, N ;
KOYAMA, M ;
SHOMURA, T ;
TSURUOKA, T ;
INOUYE, S .
JOURNAL OF ANTIBIOTICS, 1983, 36 (10) :1263-1267