链霉菌K15 DD-肽酶与自杀性β-内酰胺羰基供体的催化反应。
Streptomyces K15 DD-peptidase-catalysed reactions with suicide beta-lactam carbonyl donors.
作者信息
Leyh-Bouille M, Nguyen-Distèche M, Pirlot S, Veithen A, Bourguignon C, Ghuysen J M
出版信息
Biochem J. 1986 Apr 1;235(1):177-82. doi: 10.1042/bj2350177.
Abstract
The values of the kinetic parameters that govern the interactions between the Streptomyces K15 DD-peptidase and beta-lactam compounds were determined by measuring the inactivating effect that these compounds exert on the transpeptidase activity of the enzyme and, in the case of [14C]benzylpenicillin and [14C]cefoxitin, by measuring the amounts of acyl-enzyme formed during the reaction. K15 DD-peptidase binds benzylpenicillin or cefoxitin at a molar ratio of 1:1. Benzylpenicilloate is the major product released during breakdown of the acyl-enzyme formed with benzylpenicillin. Benzylpenicillin is not a better acylating agent than the amide Ac2-L-Lys-D-Ala-D-Ala and ester Ac2-L-Lys-D-Ala-D-lactatecarbonyl-donor substrates. beta-Lactam compounds possessing a methoxy group on the alpha-face of the molecule show high inactivating potency.
摘要
通过测量这些化合物对该酶转肽酶活性的失活作用，以及在[14C]苄青霉素和[14C]头孢西丁的情况下，通过测量反应过程中形成的酰基酶的量，确定了控制链霉菌K15 DD-肽酶与β-内酰胺化合物之间相互作用的动力学参数值。K15 DD-肽酶以1:1的摩尔比结合苄青霉素或头孢西丁。苄青霉素酸酯是在与苄青霉素形成的酰基酶分解过程中释放的主要产物。苄青霉素不是比酰胺Ac2-L-Lys-D-Ala-D-Ala和酯Ac2-L-Lys-D-Ala-D-乳酸羰基供体底物更好的酰化剂。在分子α面具有甲氧基的β-内酰胺化合物显示出高失活效力。
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本文引用的文献
1
The use of intensifying screens or organic scintillators for visualizing radioactive molecules resolved by gel electrophoresis.使用增感屏或有机闪烁体来可视化通过凝胶电泳分离的放射性分子。
Methods Enzymol. 1980;65(1):363-71. doi: 10.1016/s0076-6879(80)65047-2.
2
Isolation of the membrane-bound 26 000-Mr penicillin-binding protein of Streptomyces strain K15 in the form of a penicillin-sensitive D-alanyl-D-alanine-cleaving transpeptidase.以青霉素敏感的D-丙氨酰-D-丙氨酸裂解转肽酶形式分离链霉菌K15菌株的膜结合26000道尔顿青霉素结合蛋白。
Biochem J. 1982 Oct 1;207(1):109-15. doi: 10.1042/bj2070109.
3
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Eur J Biochem. 1982 Jun;124(3):507-12. doi: 10.1111/j.1432-1033.1982.tb06622.x.
4
Binding of monobactams to penicillin-binding proteins of Escherichia coli and Staphylococcus aureus: relation to antibacterial activity.单环β-内酰胺类抗生素与大肠杆菌和金黄色葡萄球菌青霉素结合蛋白的结合：与抗菌活性的关系。
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5
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Philos Trans R Soc Lond B Biol Sci. 1980 May 16;289(1036):257-71. doi: 10.1098/rstb.1980.0044.
6
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7
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8
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