荧光素标记青霉素的合成、纯化及动力学性质
Synthesis, purification and kinetic properties of fluorescein-labelled penicillins.
作者信息
Lakaye B, Damblon C, Jamin M, Galleni M, Lepage S, Joris B, Marchand-Brynaert J, Frydrych C, Frere J M
机构信息
Laboratoire d'Enzymologie and Centre d'ingénierie des protéines, Université de Liège, Sart-Tilman, Belgium.
出版信息
Biochem J. 1994 May 15;300 ( Pt 1)(Pt 1):141-5. doi: 10.1042/bj3000141.
Abstract
The synthesis and properties of six fluorescein-labelled penicillins are reported. The two isomers of fluoresceyl-glycyl-6-amino-penicillanic acid are probably the best compounds to use for detection of all the penicillin-binding proteins (PBPs) present in a bacterial membrane preparation. However, the derivatives of ampicillin were much more efficient against Enterobacter aerogenes PBP3. The two isomers obtained when a commercial mixture of the two isomers of carboxyfluorescein was used most often exhibited similar properties, but the Streptomyces R61 extracellular DD-peptidase was only efficiently acylated by the 5'-carboxyfluorescein derivative of glycyl-6-aminopenicillanic acid.
摘要
报道了六种荧光素标记青霉素的合成及性质。荧光素基甘氨酰-6-氨基青霉烷酸的两种异构体可能是用于检测细菌膜制剂中所有青霉素结合蛋白（PBPs）的最佳化合物。然而，氨苄西林的衍生物对产气肠杆菌PBP3的作用效率更高。当使用羧基荧光素两种异构体的商业混合物时得到的两种异构体通常表现出相似的性质，但链霉菌R61细胞外DD-肽酶仅被甘氨酰-6-氨基青霉烷酸的5'-羧基荧光素衍生物有效酰化。
相似文献
1
Synthesis, purification and kinetic properties of fluorescein-labelled penicillins.荧光素标记青霉素的合成、纯化及动力学性质
Biochem J. 1994 May 15;300 ( Pt 1)(Pt 1):141-5. doi: 10.1042/bj3000141.
2
Kinetic properties of the Bacillus licheniformis penicillin-binding proteins.
Biochem J. 1995 Jul 1;309 ( Pt 1)(Pt 1):49-53. doi: 10.1042/bj3090049.
3
A new, highly sensitive method for the detection and quantification of penicillin-binding proteins.一种用于检测和定量青霉素结合蛋白的新型高灵敏度方法。
Biochem J. 1993 Apr 1;291 ( Pt 1)(Pt 1):19-21. doi: 10.1042/bj2910019.
4
Purification of Streptococcus faecium penicillin binding protein 5, a multifunctional penicillin-binding protein.
Microbiologica. 1986 Jan;9(1):21-8.
5
Application of a charge/size two-dimensional gel electrophoresis system to the analysis of the penicillin-binding proteins of Escherichia coli.电荷/大小二维凝胶电泳系统在大肠杆菌青霉素结合蛋白分析中的应用。
FEBS Lett. 1984 Mar 12;168(1):93-6. doi: 10.1016/0014-5793(84)80213-6.
6
Changes in penicillin-binding proteins during the life cycle of Micromonospora.小单孢菌生命周期中青霉素结合蛋白的变化
Microbiologica. 1987 Apr;10(2):229-34.
7
Penicillin-binding proteins in Borrelia burgdorferi.伯氏疏螺旋体中的青霉素结合蛋白
J Bacteriol. 1990 Oct;172(10):6139-41. doi: 10.1128/jb.172.10.6139-6141.1990.
8
Transcriptional analysis of the DD-peptidase/penicillin-binding protein-encoding dac gene of Streptomyces R61: use of the promoter and signal sequences in a secretion vector.链霉菌R61的DD-肽酶/青霉素结合蛋白编码dac基因的转录分析：分泌载体中启动子和信号序列的应用
Mol Gen Genet. 1990 Aug;223(1):114-20. doi: 10.1007/BF00315803.
9
Interaction of (2,3)-methylenepenams with penicillin-binding proteins.（2,3）-亚甲基青霉烯与青霉素结合蛋白的相互作用。
Antimicrob Agents Chemother. 1987 Jul;31(7):1069-74. doi: 10.1128/AAC.31.7.1069.
10
Membrane topology, structure, and functions of the penicillin-interactive proteins.青霉素相互作用蛋白的膜拓扑结构、结构及功能
Biotechnol Appl Biochem. 1990 Oct;12(5):468-72.
引用本文的文献
1
Dismantling the bacterial glycocalyx: Chemical tools to probe, perturb, and image bacterial glycans.细菌糖萼的解体：用于探测、干扰和成像细菌聚糖的化学工具。
Bioorg Med Chem. 2021 Jul 15;42:116268. doi: 10.1016/j.bmc.2021.116268. Epub 2021 Jun 7.
2
The bacterial cell division protein fragment FtsN binds to and activates the major peptidoglycan synthase PBP1b.细菌细胞分裂蛋白片段 FtsN 与主要肽聚糖合成酶 PBP1b 结合并激活它。
J Biol Chem. 2020 Dec 25;295(52):18256-18265. doi: 10.1074/jbc.RA120.015951. Epub 2020 Oct 27.
3
Chemical tools for selective activity profiling of bacterial penicillin-binding proteins.用于细菌青霉素结合蛋白选择性活性分析的化学工具。
Methods Enzymol. 2020;638:27-55. doi: 10.1016/bs.mie.2020.02.015. Epub 2020 Apr 28.
4
Regulation of the Peptidoglycan Polymerase Activity of PBP1b by Antagonist Actions of the Core Divisome Proteins FtsBLQ and FtsN.通过核心分裂体蛋白 FtsBLQ 和 FtsN 的拮抗作用调节 PBP1b 的肽聚糖聚合酶活性。
mBio. 2019 Jan 8;10(1):e01912-18. doi: 10.1128/mBio.01912-18.
5
Novel Electrophilic Scaffold for Imaging of Essential Penicillin-Binding Proteins in Streptococcus pneumoniae.用于肺炎链球菌中必需青霉素结合蛋白成像的新型亲电支架
ACS Chem Biol. 2017 Nov 17;12(11):2849-2857. doi: 10.1021/acschembio.7b00614. Epub 2017 Oct 18.
6
Interplay between Penicillin-binding proteins and SEDS proteins promotes bacterial cell wall synthesis.青霉素结合蛋白与 SEDS 蛋白之间的相互作用促进了细菌细胞壁的合成。
Sci Rep. 2017 Feb 24;7:43306. doi: 10.1038/srep43306.
7
Cell-wall remodeling drives engulfment during sporulation.细胞壁重塑在孢子形成过程中驱动吞噬作用。
Elife. 2016 Nov 17;5:e18657. doi: 10.7554/eLife.18657.
8
Development of new drugs for an old target: the penicillin binding proteins.开发针对老靶点的新药：青霉素结合蛋白。
Molecules. 2012 Oct 24;17(11):12478-505. doi: 10.3390/molecules171112478.
9
Selective penicillin-binding protein imaging probes reveal substructure in bacterial cell division.选择性青霉素结合蛋白成像探针揭示细菌细胞分裂中的亚结构。
ACS Chem Biol. 2012 Oct 19;7(10):1746-53. doi: 10.1021/cb300329r. Epub 2012 Aug 21.
10
New noncovalent inhibitors of penicillin-binding proteins from penicillin-resistant bacteria.耐青霉素细菌的青霉素结合蛋白的新型非共价抑制剂。
PLoS One. 2011 May 9;6(5):e19418. doi: 10.1371/journal.pone.0019418.
本文引用的文献
1
Penicillin binding protein 2x as a major contributor to intrinsic beta-lactam resistance of Streptococcus pneumoniae.青霉素结合蛋白2x是肺炎链球菌固有β-内酰胺耐药性的主要促成因素。
FEBS Lett. 1993 Sep 27;331(1-2):101-4. doi: 10.1016/0014-5793(93)80305-e.
2
A new, highly sensitive method for the detection and quantification of penicillin-binding proteins.一种用于检测和定量青霉素结合蛋白的新型高灵敏度方法。
Biochem J. 1993 Apr 1;291 ( Pt 1)(Pt 1):19-21. doi: 10.1042/bj2910019.
3
Penicillin-binding protein 2x of Streptococcus pneumoniae: enzymic activities and interactions with beta-lactams.肺炎链球菌的青霉素结合蛋白2x：酶活性及与β-内酰胺类药物的相互作用
Biochem J. 1993 Jun 15;292 ( Pt 3)(Pt 3):735-41. doi: 10.1042/bj2920735.
4
Interaction between non-classical beta-lactam compounds and the Zn2+-containing G and serine R61 and R39 D-alanyl-D-alanine peptidases.非经典β-内酰胺化合物与含锌的G型和丝氨酸R61及R39 D-丙氨酰-D-丙氨酸肽酶之间的相互作用。
Biochem J. 1981 Oct 1;199(1):129-36. doi: 10.1042/bj1990129.
5
Resistance of Escherichia coli to penicillins. VI. Purification and characterization of the chromosomally mediated penicillinase present in ampA-containing strains.大肠杆菌对青霉素的耐药性。VI. 含ampA菌株中染色体介导的青霉素酶的纯化及特性分析。
J Bacteriol. 1970 Jan;101(1):218-31. doi: 10.1128/jb.101.1.218-231.1970.
6
Fluorescence and circular dichroism studies on the Streptomyces R61 DD-carboxypeptidase-transpeptidase. Penicillin binding by the enzyme.链霉菌R61 D-羧肽酶-转肽酶的荧光和圆二色性研究。该酶与青霉素的结合。
Biochem J. 1973 Nov;135(3):493-505. doi: 10.1042/bj1350493.
7
Molecular weight, amino acid composition and physicochemical properties of the exocellular DD-carboxypeptidase-transpeptidase of Streptomyces R39.链霉菌R39胞外DD-羧肽酶-转肽酶的分子量、氨基酸组成及理化性质
Biochem J. 1974 Oct;143(1):233-40. doi: 10.1042/bj1430233.
8
Interaction between beta-lactam antibiotics and exocellular DD-carboxypeptidase-transpeptidase of Streptomyces R61.β-内酰胺抗生素与链霉菌R61的胞外DD-羧肽酶-转肽酶之间的相互作用。
Eur J Biochem. 1974 Dec 16;50(1):203-14. doi: 10.1111/j.1432-1033.1974.tb03889.x.
9
Penicillin-sensitive enzymes in peptidoglycan biosynthesis.肽聚糖生物合成中对青霉素敏感的酶。
Crit Rev Microbiol. 1985;11(4):299-396. doi: 10.3109/10408418409105906.
10
The pH dependence of the active-site serine DD-peptidase of Streptomyces R61.链霉菌R61活性位点丝氨酸DD-肽酶的pH依赖性
Eur J Biochem. 1987 Feb 2;162(3):525-31. doi: 10.1111/j.1432-1033.1987.tb10671.x.
Zotero 插件