枯草芽孢杆菌ATCC6633产生的抗真菌膦酸酯寡肽根霉素的生物合成。
Biosynthesis of rhizocticins, antifungal phosphonate oligopeptides produced by Bacillus subtilis ATCC6633.
作者信息
Borisova Svetlana A, Circello Benjamin T, Zhang Jun Kai, van der Donk Wilfred A, Metcalf William W
机构信息
Institute for Genomic Biology, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA.
出版信息
Chem Biol. 2010 Jan 29;17(1):28-37. doi: 10.1016/j.chembiol.2009.11.017.
Abstract
Rhizocticins are phosphonate oligopeptide antibiotics containing the C-terminal nonproteinogenic amino acid (Z)-l-2-amino-5-phosphono-3-pentenoic acid (APPA). Here we report the identification and characterization of the rhizocticin biosynthetic gene cluster (rhi) in Bacillus subtilis ATCC6633. Rhizocticin B was heterologously produced in the nonproducer strain Bacillus subtilis 168. A biosynthetic pathway is proposed on the basis of bioinformatics analysis of the rhi genes. One of the steps during the biosynthesis of APPA is an unusual aldol reaction between phosphonoacetaldehyde and oxaloacetate catalyzed by an aldolase homolog RhiG. Recombinant RhiG was prepared, and the product of an in vitro enzymatic conversion was characterized. Access to this intermediate allows for biochemical characterization of subsequent steps in the pathway.
摘要
根瘤菌素是一类膦酸酯寡肽抗生素，其C末端含有非蛋白质ogenic氨基酸(Z)-l-2-氨基-5-膦酰基-3-戊烯酸(APPA)。在此，我们报道了枯草芽孢杆菌ATCC6633中根瘤菌素生物合成基因簇(rhi)的鉴定和表征。根瘤菌素B在非产生菌枯草芽孢杆菌168中异源产生。基于rhi基因的生物信息学分析，提出了一条生物合成途径。APPA生物合成过程中的一个步骤是由醛缩酶同源物RhiG催化的膦酰乙醛和草酰乙酸之间的异常醛醇反应。制备了重组RhiG，并对体外酶促转化产物进行了表征。获得该中间体有助于对该途径后续步骤进行生化表征。
相似文献
1
Biosynthesis of rhizocticins, antifungal phosphonate oligopeptides produced by Bacillus subtilis ATCC6633.枯草芽孢杆菌ATCC6633产生的抗真菌膦酸酯寡肽根霉素的生物合成。
Chem Biol. 2010 Jan 29;17(1):28-37. doi: 10.1016/j.chembiol.2009.11.017.
2
Molecular Basis of Bacillus subtilis ATCC 6633 Self-Resistance to the Phosphono-oligopeptide Antibiotic Rhizocticin.枯草芽孢杆菌 ATCC 6633 自身抗磷酸寡肽抗生素雷索霉素的分子基础。
ACS Chem Biol. 2019 Apr 19;14(4):742-750. doi: 10.1021/acschembio.9b00030. Epub 2019 Mar 13.
3
Rhizocticin A, an antifungal phosphono-oligopeptide of Bacillus subtilis ATCC 6633: biological properties.根际霉素A，一种枯草芽孢杆菌ATCC 6633产生的抗真菌膦酰基寡肽：生物学特性
Arch Microbiol. 1990;153(3):276-81. doi: 10.1007/BF00249082.
4
Molecular cloning and heterologous expression of the dehydrophos biosynthetic gene cluster.脱氢磷生物合成基因簇的分子克隆与异源表达
Chem Biol. 2010 Apr 23;17(4):402-11. doi: 10.1016/j.chembiol.2010.03.007.
5
Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizocticin A and Plumbemycin A.潜在苏氨酸合酶抑制剂的合成与生物评价：雷地霉素 A 和铅霉素 A。
Bioorg Med Chem. 2013 Sep 1;21(17):4958-67. doi: 10.1016/j.bmc.2013.06.064. Epub 2013 Jul 8.
6
Digestion of rhizocticins to (Z)-L-2-amino-5-phosphono-3-pentenoic acid: revision of the absolute configuration of plumbemycins A and B.根霉毒素消化生成（Z）-L-2-氨基-5-膦酰基-3-戊烯酸：铅霉素A和B的绝对构型修正
J Antibiot (Tokyo). 1995 Sep;48(9):1043-5. doi: 10.7164/antibiotics.48.1043.
7
A novel L-amino acid ligase from Bacillus subtilis NBRC3134, a microorganism producing peptide-antibiotic rhizocticin.一种来自枯草芽孢杆菌NBRC3134的新型L-氨基酸连接酶，该菌株是一种能产生肽抗生素根瘤菌素的微生物。
Biosci Biotechnol Biochem. 2009 Apr 23;73(4):901-7. doi: 10.1271/bbb.80842. Epub 2009 Apr 7.
8
Identification of a second oligopeptide transport system in Bacillus subtilis and determination of its role in sporulation.枯草芽孢杆菌中第二种寡肽转运系统的鉴定及其在芽孢形成中的作用测定。
Mol Microbiol. 1994 Aug;13(3):417-26. doi: 10.1111/j.1365-2958.1994.tb00436.x.
9
Isolation of a gene essential for biosynthesis of the lipopeptide antibiotics plipastatin B1 and surfactin in Bacillus subtilis YB8.枯草芽孢杆菌YB8中脂肽抗生素普利他汀B1和表面活性素生物合成必需基因的分离
Arch Microbiol. 1996 Apr;165(4):243-51. doi: 10.1007/s002030050322.
10
The mycosubtilin synthetase of Bacillus subtilis ATCC6633: a multifunctional hybrid between a peptide synthetase, an amino transferase, and a fatty acid synthase.枯草芽孢杆菌ATCC6633的真菌枯草菌素合成酶：一种肽合成酶、氨基转移酶和脂肪酸合成酶之间的多功能杂合体。
Proc Natl Acad Sci U S A. 1999 Nov 9;96(23):13294-9. doi: 10.1073/pnas.96.23.13294.
引用本文的文献
1
Secondary Metabolites of from and Their Antifungal and Plant Growth-Regulating Properties.来自[具体来源未提及]的次生代谢产物及其抗真菌和植物生长调节特性
Plants (Basel). 2025 Jul 4;14(13):2058. doi: 10.3390/plants14132058.
2
Recently discovered heteromeric enzymes in natural product biosynthesis.天然产物生物合成中最近发现的异源多聚酶。
J Biol Chem. 2025 Apr 17;301(6):108516. doi: 10.1016/j.jbc.2025.108516.
3
Whole-Genome Profiling of Endophytic Strain B.L.Ns.14 from Reveals Potential for Agricultural Bioenhancement.来自[具体来源未提及]的内生菌株B.L.Ns.14的全基因组分析揭示了农业生物强化的潜力。
Microorganisms. 2024 Dec 16;12(12):2604. doi: 10.3390/microorganisms12122604.
4
Biosynthesis of Phosphonoalamides Reveals Highly Specific Amino Acid Ligation.膦酰氨类的生物合成揭示了高度特异的氨基酸连接。
ACS Chem Biol. 2024 Jul 19;19(7):1506-1514. doi: 10.1021/acschembio.4c00190. Epub 2024 Jun 17.
5
Phosphonoalamides Reveal the Biosynthetic Origin of Phosphonoalanine Natural Products and a Convergent Pathway for Their Diversification.膦酰氨类揭示了磷酰丝氨酸天然产物的生物合成起源和它们多样化的趋同途径。
Angew Chem Int Ed Engl. 2024 Aug 5;63(32):e202405052. doi: 10.1002/anie.202405052. Epub 2024 Jul 9.
6
Discovery of Antimicrobial Phosphonopeptide Natural Products from Bacillus velezensis by Genome Mining.从韦荣氏球菌属中通过基因组挖掘发现抗菌膦肽天然产物。
Appl Environ Microbiol. 2023 Jun 28;89(6):e0033823. doi: 10.1128/aem.00338-23. Epub 2023 May 31.
7
A Novel Pathway for Biosynthesis of the Herbicidal Phosphonate Natural Product Phosphonothrixin Is Widespread in Actinobacteria.一种新型生物合成途径可广泛用于产生除草膦天然产物膦丝菌素的放线菌。
J Bacteriol. 2023 May 25;205(5):e0048522. doi: 10.1128/jb.00485-22. Epub 2023 Apr 19.
8
The genome of EA-CB0015 sheds light into its epiphytic lifestyle and potential as a biocontrol agent.EA-CB0015的基因组揭示了其附生生活方式以及作为生物防治剂的潜力。
Front Microbiol. 2023 Mar 27;14:1135487. doi: 10.3389/fmicb.2023.1135487. eCollection 2023.
9
Convergent and divergent biosynthetic strategies towards phosphonic acid natural products.磷酸天然产物的汇聚和发散生物合成策略。
Curr Opin Chem Biol. 2022 Dec;71:102214. doi: 10.1016/j.cbpa.2022.102214. Epub 2022 Oct 3.
10
Highly stereoselective and enantiodivergent synthesis of cyclopropylphosphonates with engineered carbene transferases.利用工程化卡宾转移酶实现环丙基膦酸酯的高度立体选择性和对映发散性合成。
Chem Sci. 2022 Jun 6;13(29):8550-8556. doi: 10.1039/d2sc01965e. eCollection 2022 Jul 29.
本文引用的文献
1
An unusual carbon-carbon bond cleavage reaction during phosphinothricin biosynthesis.膦丝菌素生物合成过程中一种不寻常的碳-碳键断裂反应。
Nature. 2009 Jun 11;459(7248):871-4. doi: 10.1038/nature07972.
2
Biosynthesis of phosphonic and phosphinic acid natural products.膦酸和次膦酸天然产物的生物合成。
Annu Rev Biochem. 2009;78:65-94. doi: 10.1146/annurev.biochem.78.091707.100215.
3
A novel L-amino acid ligase from Bacillus subtilis NBRC3134, a microorganism producing peptide-antibiotic rhizocticin.一种来自枯草芽孢杆菌NBRC3134的新型L-氨基酸连接酶，该菌株是一种能产生肽抗生素根瘤菌素的微生物。
Biosci Biotechnol Biochem. 2009 Apr 23;73(4):901-7. doi: 10.1271/bbb.80842. Epub 2009 Apr 7.
4
Protein structure prediction on the Web: a case study using the Phyre server.网络上的蛋白质结构预测：使用Phyre服务器的案例研究
Nat Protoc. 2009;4(3):363-71. doi: 10.1038/nprot.2009.2.
5
Structure and function of the LysR-type transcriptional regulator (LTTR) family proteins.赖斯R型转录调节因子（LTTR）家族蛋白的结构与功能
Microbiology (Reading). 2008 Dec;154(Pt 12):3609-3623. doi: 10.1099/mic.0.2008/022772-0.
6
A novel l-amino acid ligase from bacillus licheniformis.
J Biosci Bioeng. 2008 Sep;106(3):313-5. doi: 10.1263/jbb.106.313.
7
Cloning, expression, and biochemical characterization of Streptomyces rubellomurinus genes required for biosynthesis of antimalarial compound FR900098.抗疟化合物FR900098生物合成所需的红褐链霉菌基因的克隆、表达及生化特性分析
Chem Biol. 2008 Aug 25;15(8):765-70. doi: 10.1016/j.chembiol.2008.07.010.
8
The putative Diels-Alderase macrophomate synthase is an efficient aldolase.假定的狄尔斯-阿尔德酶巨豆三烯酸合酶是一种高效的醛缩酶。
J Am Chem Soc. 2008 Jun 25;130(25):7798-9. doi: 10.1021/ja8017994. Epub 2008 May 31.
9
Dipeptide synthesis by L-amino acid ligase from Ralstonia solanacearum.由青枯雷尔氏菌的L-氨基酸连接酶进行的二肽合成。
Biochem Biophys Res Commun. 2008 Jul 4;371(3):536-40. doi: 10.1016/j.bbrc.2008.04.105. Epub 2008 Apr 28.
10
The RAST Server: rapid annotations using subsystems technology.RAST服务器：使用子系统技术进行快速注释。
BMC Genomics. 2008 Feb 8;9:75. doi: 10.1186/1471-2164-9-75.
Zotero 插件