通过II型非核糖体肽合成酶机制引发II型聚酮化合物合成酶。
Priming type II polyketide synthases via a type II nonribosomal peptide synthetase mechanism.
作者信息
Izumikawa Miho, Cheng Qian, Moore Bradley S
机构信息
College of Pharmacy, University of Arizona, Tucson, Arizona 85721, USA.
出版信息
J Am Chem Soc. 2006 Feb 8;128(5):1428-9. doi: 10.1021/ja0559707.
Abstract
Benzoic acid priming of the enterocin and actinorhodin type II polyketide synthase complexes was accomplished in vitro via an unprecedented type II nonribosomal peptide synthetase-like mechanism involving the benzoate:acyl carrier protein (ACP) ligase EncN and the ACP EncC. The transfer of the aryl acid to the ACP is ATP-dependent, yet coenzyme A-independent, as characterized with radiolabeled substrates and protein mass spectrometry. Subsequent transport of the ACP-bound aryl group to the native enterocin and the aberrant actinorhodin ketosynthase chain length factor heterodimers was further demonstrated, thereby demonstrating the potential of this biocatalyst for engineering diverse aryl-primed aromatic polyketide agents.
摘要
通过一种前所未有的II型非核糖体肽合成酶样机制，在体外实现了对肠球菌素和放线紫红素II型聚酮合酶复合物的苯甲酸引发，该机制涉及苯甲酸：酰基载体蛋白（ACP）连接酶EncN和ACP EncC。正如用放射性标记底物和蛋白质质谱法所表征的那样，芳酸向ACP的转移是ATP依赖性的，但不依赖辅酶A。进一步证明了与ACP结合的芳基随后向天然肠球菌素和异常的放线紫红素酮合成酶链长因子异二聚体的转移，从而证明了这种生物催化剂用于工程化多种芳基引发的芳香族聚酮化合物的潜力。
相似文献
1
Priming type II polyketide synthases via a type II nonribosomal peptide synthetase mechanism.通过II型非核糖体肽合成酶机制引发II型聚酮化合物合成酶。
J Am Chem Soc. 2006 Feb 8;128(5):1428-9. doi: 10.1021/ja0559707.
2
Characterization of the Ketosynthase and Acyl Carrier Protein Domains at the LnmI Nonribosomal Peptide Synthetase-Polyketide Synthase Interface for Leinamycin Biosynthesis.酮合酶和酰基载体蛋白结构域在 LnmI 非核糖体肽合成酶-聚酮合酶界面的表征及其在雷纳霉素生物合成中的作用。
Org Lett. 2016 Sep 2;18(17):4288-91. doi: 10.1021/acs.orglett.6b02033. Epub 2016 Aug 19.
3
Binding and "pKa" modulation of a polycyclic substrate analogue in a type II polyketide acyl carrier protein.在 II 型聚酮类酰基载体蛋白中，多环底物类似物的结合和“pKa”调节。
ACS Chem Biol. 2011 May 20;6(5):413-8. doi: 10.1021/cb200004k. Epub 2011 Feb 22.
4
Molecular recognition between ketosynthase and acyl carrier protein domains of the 6-deoxyerythronolide B synthase.酮基合成酶与 6-脱氧赤藓醇 B 合酶酰基载体蛋白结构域之间的分子识别。
Proc Natl Acad Sci U S A. 2010 Dec 21;107(51):22066-71. doi: 10.1073/pnas.1014081107. Epub 2010 Dec 2.
5
One-Step Transformation of Coenzyme A into Analogues by Transamidation.辅酶 A 通过转酰胺作用一步转化为类似物。
Org Lett. 2017 Apr 21;19(8):1950-1953. doi: 10.1021/acs.orglett.7b00291. Epub 2017 Apr 10.
6
First in vitro directed biosynthesis of new compounds by a minimal type II polyketide synthase: evidence for the mechanism of chain length determination.
Chem Commun (Camb). 2003 Mar 21(6):686-7. doi: 10.1039/b300847a.
7
The malonyl transferase activity of type II polyketide synthase acyl carrier proteins.II型聚酮合酶酰基载体蛋白的丙二酰转移酶活性
Chem Biol. 2006 Jun;13(6):587-96. doi: 10.1016/j.chembiol.2006.03.010.
8
Purification, priming, and catalytic acylation of carrier protein domains in the polyketide synthase and nonribosomal peptidyl synthetase modules of the HMWP1 subunit of yersiniabactin synthetase.耶尔森菌素合成酶HMWP1亚基的聚酮合酶和非核糖体肽基合成酶模块中载体蛋白结构域的纯化、引发及催化酰化作用
Proc Natl Acad Sci U S A. 2001 Jan 2;98(1):99-104. doi: 10.1073/pnas.98.1.99.
9
Policing starter unit selection of the enterocin type II polyketide synthase by the type II thioesterase EncL.肠球菌素 II 型聚酮合酶由 II 型硫酯酶 EncL 引发单元选择的 policing。
Bioorg Med Chem. 2011 Nov 15;19(22):6633-8. doi: 10.1016/j.bmc.2011.04.024. Epub 2011 Apr 16.
10
Probing the Interactions of early polyketide intermediates with the Actinorhodin ACP from S. coelicolor A3(2).探究早期聚酮化合物中间体与天蓝色链霉菌A3(2)的放线紫红素酰基载体蛋白之间的相互作用。
J Mol Biol. 2009 Jun 12;389(3):511-28. doi: 10.1016/j.jmb.2009.03.072. Epub 2009 Apr 8.
引用本文的文献
1
Structural comparison of Acinetobacter baumannii β-ketoacyl-acyl carrier protein reductases in fatty acid and aryl polyene biosynthesis.鲍曼不动杆菌β-酮酰-酰基辅酶 A 还原酶在脂肪酸和芳基聚烯生物合成中的结构比较。
Sci Rep. 2021 Apr 12;11(1):7945. doi: 10.1038/s41598-021-86997-3.
2
Marinoterpins A-C: Rare Linear Merosesterterpenoids from Marine-Derived Actinomycete Bacteria of the Family Streptomycetaceae.马林萜 A-C：来自海洋放线菌科链霉菌属海洋衍生放线菌的罕见线性单萜。
J Org Chem. 2021 Aug 20;86(16):11140-11148. doi: 10.1021/acs.joc.1c00262. Epub 2021 Apr 12.
3
Cell-free synthetic biology for biosynthesis of pharmaceutical natural products.用于药物天然产物生物合成的无细胞合成生物学
Synth Syst Biotechnol. 2018 Feb 17;3(2):83-89. doi: 10.1016/j.synbio.2018.02.002. eCollection 2018 Jun.
4
Polyketide genes in the marine sponge Plakortis simplex: a new group of mono-modular type I polyketide synthases from sponge symbionts.海洋海绵 Plakortis simplex 中的聚酮基因：一类来自海绵共生体的新型单模块 I 型聚酮合酶。
Environ Microbiol Rep. 2013 Dec;5(6):809-18. doi: 10.1111/1758-2229.12081. Epub 2013 Jul 25.
5
Flavin-mediated dual oxidation controls an enzymatic Favorskii-type rearrangement.黄素介导的双重氧化控制酶促 Favorskii 重排。
Nature. 2013 Nov 28;503(7477):552-556. doi: 10.1038/nature12643. Epub 2013 Oct 27.
6
Policing starter unit selection of the enterocin type II polyketide synthase by the type II thioesterase EncL.肠球菌素 II 型聚酮合酶由 II 型硫酯酶 EncL 引发单元选择的 policing。
Bioorg Med Chem. 2011 Nov 15;19(22):6633-8. doi: 10.1016/j.bmc.2011.04.024. Epub 2011 Apr 16.
7
Total (bio)synthesis: strategies of nature and of chemists.全（生物）合成：自然与化学家的策略
Top Curr Chem. 2010;297:149-203. doi: 10.1007/128_2010_79.
8
Biosynthesis of aromatic polyketides in bacteria.细菌中芳香聚酮化合物的生物合成。
Acc Chem Res. 2009 May 19;42(5):631-9. doi: 10.1021/ar8002249.
9
In vitro biosynthesis of unnatural enterocin and wailupemycin polyketides.在体外生物合成非天然肠球菌素和沃拉普霉素聚酮化合物。
J Nat Prod. 2009 Mar 27;72(3):469-72. doi: 10.1021/np800598t.
10
Accessing natural product biosynthetic processes by mass spectrometry.通过质谱法研究天然产物生物合成过程
Curr Opin Chem Biol. 2008 Oct;12(5):475-82. doi: 10.1016/j.cbpa.2008.07.022.
本文引用的文献
1
Production of branched-chain alkylprodiginines in S. coelicolor by replacement of the 3-ketoacyl ACP synthase III initiation enzyme, RedP.通过替换3-酮酰基ACP合酶III起始酶RedP在天蓝色链霉菌中生产支链烷基灵菌红素
Chem Biol. 2005 Feb;12(2):191-200. doi: 10.1016/j.chembiol.2004.11.006.
2
EncM, a versatile enterocin biosynthetic enzyme involved in Favorskii oxidative rearrangement, aldol condensation, and heterocycle-forming reactions.EncM是一种多功能肠球菌生物合成酶，参与法沃斯基氧化重排、羟醛缩合和杂环形成反应。
Proc Natl Acad Sci U S A. 2004 Nov 2;101(44):15609-14. doi: 10.1073/pnas.0405508101. Epub 2004 Oct 25.
3
Context-dependent behavior of the enterocin iterative polyketide synthase; a new model for ketoreduction.肠球菌迭代聚酮合酶的上下文依赖性行为；酮还原的新模型。
Chem Biol. 2004 Apr;11(4):461-8. doi: 10.1016/j.chembiol.2004.03.018.
4
The blasticidin S biosynthesis gene cluster from Streptomyces griseochromogenes: sequence analysis, organization, and initial characterization.灰色产色链霉菌中杀稻瘟菌素S生物合成基因簇：序列分析、结构及初步表征
Chembiochem. 2003 Sep 5;4(9):821-8. doi: 10.1002/cbic.200300583.
5
Mutasynthesis of enterocin and wailupemycin analogues.肠球菌素和瓦卢皮霉素类似物的突变生物合成
J Am Chem Soc. 2003 Aug 6;125(31):9290-1. doi: 10.1021/ja035973o.
6
First in vitro directed biosynthesis of new compounds by a minimal type II polyketide synthase: evidence for the mechanism of chain length determination.
Chem Commun (Camb). 2003 Mar 21(6):686-7. doi: 10.1039/b300847a.
7
Characterization of benzoyl coenzyme A biosynthesis genes in the enterocin-producing bacterium "Streptomyces maritimus".产肠球菌素的细菌“海链霉菌”中苯甲酰辅酶A生物合成基因的表征
J Bacteriol. 2003 Jan;185(2):399-404. doi: 10.1128/JB.185.2.399-404.2003.
8
Inactivation, complementation, and heterologous expression of encP, a novel bacterial phenylalanine ammonia-lyase gene.新型细菌苯丙氨酸解氨酶基因encP的失活、互补及异源表达
J Biol Chem. 2002 Sep 6;277(36):32505-9. doi: 10.1074/jbc.M204171200. Epub 2002 Jun 24.
9
The loading and initial elongation modules of rifamycin synthetase collaborate to produce mixed aryl ketide products.利福霉素合成酶的负载和初始延伸模块协同作用以产生混合芳基酮化物产物。
Biochemistry. 2002 Apr 23;41(16):5313-24. doi: 10.1021/bi0200312.
10
A mechanism of benzoic acid biosynthesis in plants and bacteria that mirrors fatty acid beta-oxidation.植物和细菌中苯甲酸生物合成的一种机制，类似于脂肪酸β-氧化。
Chembiochem. 2001 Oct 1;2(10):784-6. doi: 10.1002/1439-7633(20011001)2:10<784::AID-CBIC784>3.0.CO;2-K.
Zotero 插件