绿脓杆菌铁载体绿脓菌素的合成及生物活性
Synthesis and biological activity of pyochelin, a siderophore of Pseudomonas aeruginosa.
作者信息
Ankenbauer R G, Toyokuni T, Staley A, Rinehart K L, Cox C D
机构信息
Department of Microbiology, University of Iowa, Iowa City 52242.
出版信息
J Bacteriol. 1988 Nov;170(11):5344-51. doi: 10.1128/jb.170.11.5344-5351.1988.
Abstract
Pyochelin, a phenolic siderophore of Pseudomonas aeruginosa, was synthesized in three steps from salicylonitrile, L-cysteine, and L-N-methylcysteine. The synthetic product was determined to be identical to natural pyochelin by 1H nuclear magnetic resonance spectroscopy, fast atom bombardment mass spectrometry, chromatographic analysis, and chemical reactivity with FeCl3 and ammoniacal silver nitrate reagent. Synthetic and natural pyochelin promoted bacterial growth in iron-depleted medium and were also found to mediate iron transport by P. aeruginosa to the same levels. Neopyochelin, a stereoisomeric by-product of the synthesis, showed less biological activity than did pyochelin in iron transport assays.
摘要
绿脓菌素是铜绿假单胞菌的一种酚类铁载体，由水杨腈、L-半胱氨酸和L-N-甲基半胱氨酸分三步合成。通过1H核磁共振光谱、快原子轰击质谱、色谱分析以及与FeCl3和氨性硝酸银试剂的化学反应性，确定合成产物与天然绿脓菌素相同。合成的绿脓菌素和天然绿脓菌素在缺铁培养基中均能促进细菌生长，并且还发现它们介导铜绿假单胞菌的铁转运至相同水平。新绿脓菌素是合成过程中的一种立体异构副产物，在铁转运试验中显示出比绿脓菌素更低的生物活性。
相似文献
1
Synthesis and biological activity of pyochelin, a siderophore of Pseudomonas aeruginosa.绿脓杆菌铁载体绿脓菌素的合成及生物活性
J Bacteriol. 1988 Nov;170(11):5344-51. doi: 10.1128/jb.170.11.5344-5351.1988.
2
Mutasynthesis of siderophore analogues by Pseudomonas aeruginosa.铜绿假单胞菌对铁载体类似物的突变生物合成
Proc Natl Acad Sci U S A. 1991 Mar 1;88(5):1878-82. doi: 10.1073/pnas.88.5.1878.
3
Bacterial siderophores: synthesis and biological activities of novel pyochelin analogues.细菌铁载体：新型绿脓菌素类似物的合成及生物活性
Bioorg Med Chem Lett. 2003 Mar 24;13(6):1147-50. doi: 10.1016/s0960-894x(03)00010-6.
4
Pseudomonas fluorescens CHA0 produces enantio-pyochelin, the optical antipode of the Pseudomonas aeruginosa siderophore pyochelin.荧光假单胞菌CHA0产生对映体螯铁菌素，即铜绿假单胞菌铁载体螯铁菌素的旋光对映体。
J Biol Chem. 2007 Dec 7;282(49):35546-53. doi: 10.1074/jbc.M707039200. Epub 2007 Oct 15.
5
Isolation and characterization of Pseudomonas aeruginosa mutants requiring salicylic acid for pyochelin biosynthesis.绿脓杆菌突变体的分离与特性研究：这些突变体在绿脓菌素生物合成过程中需要水杨酸。
J Bacteriol. 1988 Nov;170(11):5364-7. doi: 10.1128/jb.170.11.5364-5367.1988.
6
Cloning of the outer membrane high-affinity Fe(III)-pyochelin receptor of Pseudomonas aeruginosa.铜绿假单胞菌外膜高亲和力铁（III）-绿脓菌素受体的克隆
J Bacteriol. 1992 Jul;174(13):4401-9. doi: 10.1128/jb.174.13.4401-4409.1992.
7
Crystal structure at high resolution of ferric-pyochelin and its membrane receptor FptA from Pseudomonas aeruginosa.铜绿假单胞菌铁载体-绿脓菌素及其膜受体FptA的高分辨率晶体结构
J Mol Biol. 2005 Sep 30;352(4):893-904. doi: 10.1016/j.jmb.2005.08.004.
8
Siderophore synthesis by mucoid Pseudomonas aeruginosa strains isolated from cystic fibrosis patients.从囊性纤维化患者中分离出的黏液型铜绿假单胞菌菌株的铁载体合成。
Can J Microbiol. 1991 Aug;37(8):654-7. doi: 10.1139/m91-111.
9
Metal regulation of siderophore synthesis in Pseudomonas aeruginosa and functional effects of siderophore-metal complexes.铜绿假单胞菌中铁载体合成的金属调控及铁载体-金属复合物的功能效应
Appl Environ Microbiol. 1992 Sep;58(9):2886-93. doi: 10.1128/aem.58.9.2886-2893.1992.
10
Essential PchG-dependent reduction in pyochelin biosynthesis of Pseudomonas aeruginosa.铜绿假单胞菌中依赖于PchG的绿脓菌素生物合成的必需减少。
J Bacteriol. 2001 Feb;183(3):813-20. doi: 10.1128/JB.183.3.813-820.2001.
引用本文的文献
1
Comprehensive genomic analysis of Burkholderia arboris PN-1 reveals its biocontrol potential against Fusarium solani-induced root rot in Panax notoginseng.全面的基因组分析揭示了鲍氏不动杆菌 PN-1 对三七土传枯萎病病原菌尖孢镰刀菌的生物防治潜力。
Curr Genet. 2024 Mar 30;70(1):4. doi: 10.1007/s00294-024-01288-4.
2
The diversity and utility of arylthiazoline and aryloxazoline siderophores: challenges of total synthesis.芳基噻唑啉和芳基恶唑啉铁载体的多样性与实用性：全合成面临的挑战
RSC Adv. 2022 Sep 7;12(39):25284-25322. doi: 10.1039/d2ra03841b. eCollection 2022 Sep 5.
3
Mining Public Mass Spectrometry Data to Characterize the Diversity and Ubiquity of Specialized Metabolites.挖掘公开的质谱数据以表征特殊代谢物的多样性和普遍性。
Metabolites. 2020 Nov 5;10(11):445. doi: 10.3390/metabo10110445.
4
Intraspecies Signaling between Common Variants of Pseudomonas aeruginosa Increases Production of Quorum-Sensing-Controlled Virulence Factors.铜绿假单胞菌常见变异株种内信号传递增加群体感应控制毒力因子的产生。
mBio. 2020 Aug 25;11(4):e01865-20. doi: 10.1128/mBio.01865-20.
5
Intermicrobial interaction: Aspergillus fumigatus siderophores protect against competition by Pseudomonas aeruginosa.微生物间相互作用：烟曲霉的铁载体可抵御铜绿假单胞菌的竞争。
PLoS One. 2019 May 8;14(5):e0216085. doi: 10.1371/journal.pone.0216085. eCollection 2019.
6
Pseudomonas aeruginosa adapts its iron uptake strategies in function of the type of infections.铜绿假单胞菌会根据感染类型调整其铁摄取策略。
Front Cell Infect Microbiol. 2013 Nov 14;3:75. doi: 10.3389/fcimb.2013.00075. eCollection 2013.
7
Identification of Burkholderia cenocepacia strain H111 virulence factors using nonmammalian infection hosts.利用非哺乳动物感染宿主鉴定洋葱伯克霍尔德菌 H111 菌株的毒力因子。
Infect Immun. 2013 Jan;81(1):143-53. doi: 10.1128/IAI.00768-12. Epub 2012 Oct 22.
8
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.
9
Stereospecificity of the siderophore pyochelin outer membrane transporters in fluorescent pseudomonads.荧光假单胞菌中铁载体绿脓菌素外膜转运蛋白的立体特异性
J Biol Chem. 2009 May 29;284(22):14949-57. doi: 10.1074/jbc.M900606200. Epub 2009 Mar 17.
10
Synthesis of carbapyochelins via diastereoselective azidation of 5-(ethoxycarbonyl)methylproline derivatives.通过5-(乙氧羰基)甲基脯氨酸衍生物的非对映选择性叠氮化反应合成碳硼螯合剂。
J Org Chem. 2008 Sep 19;73(18):7420-3. doi: 10.1021/jo801294p. Epub 2008 Aug 13.
本文引用的文献
1
A plasmid associated with virulence in the marine fish pathogen Vibrio anguillarum specifies an iron-sequestering system.与海洋鱼类病原体鳗弧菌毒力相关的一种质粒规定了一种铁螯合系统。
Nature. 1980 Apr 10;284(5756):566-8. doi: 10.1038/284566a0.
2
The significance of iron in infection.铁在感染中的意义。
Rev Infect Dis. 1981 Nov-Dec;3(6):1127-38. doi: 10.1093/clinids/3.6.1127.
3
Pseudomonas aeruginosa mutants altered in their sensitivity to the effect of iron on toxin A or elastase yields.铜绿假单胞菌突变体对铁对毒素A或弹性蛋白酶产量影响的敏感性发生改变。
J Bacteriol. 1982 Aug;151(2):783-7. doi: 10.1128/jb.151.2.783-787.1982.
4
Effect of pyochelin on the virulence of Pseudomonas aeruginosa.绿脓菌素对铜绿假单胞菌毒力的影响。
Infect Immun. 1982 Apr;36(1):17-23. doi: 10.1128/iai.36.1.17-23.1982.
5
Pyochelin: novel structure of an iron-chelating growth promoter for Pseudomonas aeruginosa.绿脓菌素：铜绿假单胞菌铁螯合生长促进剂的新结构
Proc Natl Acad Sci U S A. 1981 Jul;78(7):4256-60. doi: 10.1073/pnas.78.7.4256.
6
Iron uptake with ferripyochelin and ferric citrate by Pseudomonas aeruginosa.铜绿假单胞菌对铁载体和柠檬酸铁的铁摄取
J Bacteriol. 1980 May;142(2):581-7. doi: 10.1128/jb.142.2.581-587.1980.
7
Vibriobactin, a siderophore from Vibrio cholerae.霍乱弧菌素，一种来自霍乱弧菌的铁载体。
J Biol Chem. 1984 Jan 10;259(1):383-5.
8
Microbial iron compounds.微生物铁化合物。
Annu Rev Biochem. 1981;50:715-31. doi: 10.1146/annurev.bi.50.070181.003435.
9
Antibody inhibition of ferripyochelin binding to Pseudomonas aeruginosa cell envelopes.
Biochemistry. 1984 Oct 9;23(21):5076-80. doi: 10.1021/bi00316a038.
10
Iron withholding: a defense against infection and neoplasia.铁限制：一种抵御感染和肿瘤的防御机制。
Physiol Rev. 1984 Jan;64(1):65-102. doi: 10.1152/physrev.1984.64.1.65.
Zotero 插件