Twofold polyketide branching by a stereoselective enzymatic Michael addition.

作者: Daniel Heine , Srividhya Sundaram , Tom Bretschneider , Christian Hertweck

DOI: 10.1039/C5CC03085D

关键词:

摘要: The versatility of the branching module rhizoxin polyketide synthase was tested in an vitro enzyme assay with a mimic and branched (di)methylmalonyl-CoA extender units. Comparison products synthetic reference compounds revealed that is able to stereoselectively introduce two branches one step by Michael addition–lactonisation sequence, thus expanding scope previously studied PKS systems.

参考文章(30)
Bradley S Moore, Christian Hertweck, Biosynthesis and attachment of novel bacterial polyketide synthase starter units Natural Product Reports. ,vol. 19, pp. 70- 99 ,(2002) , 10.1039/B003939J
W.Clark Still, Cesare Gennari, Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination. Tetrahedron Letters. ,vol. 24, pp. 4405- 4408 ,(1983) , 10.1016/S0040-4039(00)85909-2
Christian Hertweck, Decoding and reprogramming complex polyketide assembly lines: prospects for synthetic biology Trends in Biochemical Sciences. ,vol. 40, pp. 189- 199 ,(2015) , 10.1016/J.TIBS.2015.02.001
Daniel Heine, Tom Bretschneider, Srividhya Sundaram, Christian Hertweck, Enzymatic Polyketide Chain Branching To Give Substituted Lactone, Lactam, and Glutarimide Heterocycles Angewandte Chemie. ,vol. 53, pp. 11645- 11649 ,(2014) , 10.1002/ANIE.201407282
Tom Bretschneider, Georg Zocher, Michelle Unger, Kirstin Scherlach, Thilo Stehle, Christian Hertweck, A ketosynthase homolog uses malonyl units to form esters in cervimycin biosynthesis Nature Chemical Biology. ,vol. 8, pp. 154- 161 ,(2012) , 10.1038/NCHEMBIO.746
Michael A. Fischbach, Christopher T. Walsh, Assembly-line enzymology for polyketide and nonribosomal Peptide antibiotics: logic, machinery, and mechanisms. Chemical Reviews. ,vol. 106, pp. 3468- 3496 ,(2006) , 10.1021/CR0503097
Gerald Lackner, Christian Hertweck, Impact of Endofungal Bacteria on Infection Biology, Food Safety, and Drug Development PLoS Pathogens. ,vol. 7, pp. e1002096- ,(2011) , 10.1371/JOURNAL.PPAT.1002096
TuAnh Nguyen, Keishi Ishida, Holger Jenke-Kodama, Elke Dittmann, Cristian Gurgui, Thomas Hochmuth, Stefan Taudien, Matthias Platzer, Christian Hertweck, Jörn Piel, Exploiting the mosaic structure of trans-acyltransferase polyketide synthases for natural product discovery and pathway dissection. Nature Biotechnology. ,vol. 26, pp. 225- 233 ,(2008) , 10.1038/NBT1379
Nicole Brendel, Laila P. Partida-Martinez, Kirstin Scherlach, Christian Hertweck, A cryptic PKS–NRPS gene locus in the plant commensal Pseudomonas fluorescens Pf-5 codes for the biosynthesis of an antimitotic rhizoxin complex Organic and Biomolecular Chemistry. ,vol. 5, pp. 2211- 2213 ,(2007) , 10.1039/B707762A
Chaitan Khosla, Daniel Herschlag, David E. Cane, Christopher T. Walsh, Assembly Line Polyketide Synthases: Mechanistic Insights and Unsolved Problems Biochemistry. ,vol. 53, pp. 2875- 2883 ,(2014) , 10.1021/BI500290T