Synchronous intramolecular cycloadditions of the polyene macrolactam polyketide heronamide C

被引：25

作者：

Booth, Thomas J. ^{[1
]}

Alt, Silke ^{[1
]}

Capon, Robert J. ^{[2
]}

Wilkinson, Barrie ^{[1
]}

机构：

[1] John Innes Inst, Dept Mol Microbiol, Norwich Res Pk, Norwich NR4 7UH, Norfolk, England

[2] Univ Queensland, Inst Mol Biosci, St Lucia, Qld 4072, Australia

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 38期

基金：

英国生物技术与生命科学研究理事会;

关键词：

BIOSYNTHESIS;

D O I：

10.1039/c6cc01930g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A growing number of natural products appear to arise from bio-synthetic pathways that involve pericyclic reactions. We show here that for the heronamides this can occur via two spontaneous pathways involving alternative thermal or photochemical intramolecular cycloadditions.

引用

页码：6383 / 6386

页数：4

共 18 条

[1] Biosynthesis of the Novel Macrolide Antibiotic Anthracimycin [J].

Alt, Silke ;

Wilkinson, Barrie .

ACS CHEMICAL BIOLOGY, 2015, 10 (11) :2468-2479

[2] Biosynthetic and biomimetic electrocyclizations [J].

Beaudry, CM ;

Malerich, JP ;

Trauner, D .

CHEMICAL REVIEWS, 2005, 105 (12) :4757-4778

[3] Conserved amino acid residues correlating with ketoreductase stereospecificity in modular polyketicle synthases [J].

Caffrey, P .

CHEMBIOCHEM, 2003, 4 (07) :654-657

[4] Mapping Microbial Response Metabolomes for Induced Natural Product Discovery [J].

Derewacz, Dagmara K. ;

Covington, Brett C. ;

McLean, John A. ;

Bachmann, Brian O. .

ACS CHEMICAL BIOLOGY, 2015, 10 (09) :1998-2006

[5] Biosynthesis of Macrolactam BE-14106 Involves Two Distinct PKS Systems and Amino Acid Processing Enzymes for Generation of the Aminoacyl Starter Unit [J].

Jorgensen, Hanne ;

Degnes, Kristin F. ;

Sletta, Havard ;

Fjaervik, Espen ;

Dikiy, Alexander ;

Herfindal, Lars ;

Bruheim, Per ;

Klinkenberg, Geir ;

Bredholt, Harald ;

Nygard, Gyrid ;

Doskeland, Stein O. ;

Ellingsen, Trond E. ;

Zotchev, Sergey B. .

CHEMISTRY & BIOLOGY, 2009, 16 (10) :1109-1121

[6]

Jorgenson H., 2009, APPL ENVIRON MICROB, V76, P283

[7] Stereocontrol within polyketide assembly lines [J].

Keatinge-Clay, Adrian T. .

NATURAL PRODUCT REPORTS, 2016, 33 (02) :141-149

[8] Enzyme-catalysed [4+2] cycloaddition is a key step in the biosynthesis of spinosyn A [J].

Kim, Hak Joong ;

Ruszczycky, Mark W. ;

Choi, Sei-hyun ;

Liu, Yung-nan ;

Liu, Hung-wen .

NATURE, 2011, 473 (7345) :109-112

[9] Natural Diels-Alderases: Elusive and Irresistable [J].

Klas, Kimberly ;

Tsukamoto, Sachiko ;

Sherman, David H. ;

Williams, Robert M. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (23) :11672-11685

[10] Heronamides A-C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp A biosynthetic case for synchronized tandem electrocyclization [J].

Raju, Ritesh ;

Piggott, Andrew M. ;

Conte, Melissa M. ;

Capon, Robert J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4682-4689

← 1 2 →