Terreni Marco, Ubiali Daniela, Bavaro Teodora, Pregnolato Massimo, Fernández-Lafuente Roberto, Guisán José M
Italian Biocatalysis Center, PBL Dipartimento di Chimica Farmaceutica, via Taramelli 12, Università degli Studi, I-27100, Pavia, Italy.
Appl Microbiol Biotechnol. 2007 Dec;77(3):579-87. doi: 10.1007/s00253-007-1186-3. Epub 2007 Sep 19.
The acylase from Arthrobacter viscosus was immobilized, studied in the enzymatic synthesis of some cephalosporins by kinetically controlled N-acylation (kcNa) of different cephem nuclei, and compared with the penicillin G acylase (PGA) from Escherichia coli. The reaction outcomes were dependent on the acylase microbial source and on the type of immobilization support. Generally, both enzymes, when immobilized onto hydrophilic resins such as glyoxyl-agarose (activated with aldehyde groups), displayed higher synthetic performances in comparison with hydrophobic acrylic epoxy-supports like Eupergit C. The kcNa of 7-amino cephalosporanic acid catalyzed by A. viscosus immobilized on glyoxyl-agarose afforded a quantitative conversion in 7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Delta(3)-cephem-4-carboxylic acid, a useful intermediate for the synthesis of Cefamandole and Cefonicid. Similar results were obtained in the synthesis of these cephalosporins by direct acylation of the corresponding 3'-functionalized nucleus. In these reactions, A. viscosus displayed higher synthetic performances than the PGA from E. coli.
对来自黏性节杆菌的酰基转移酶进行了固定化处理，通过对不同头孢烯核进行动力学控制的N - 酰化反应（kcNa）来研究其在某些头孢菌素酶促合成中的应用，并与来自大肠杆菌的青霉素G酰基转移酶（PGA）进行比较。反应结果取决于酰基转移酶的微生物来源和固定化载体的类型。一般来说，当将这两种酶固定在亲水性树脂（如用醛基活化的乙醛酸琼脂糖）上时，与疏水性丙烯酸环氧载体（如Eupergit C）相比，它们表现出更高的合成性能。固定在乙醛酸琼脂糖上的黏性节杆菌催化7 - 氨基头孢烷酸的kcNa反应，可定量转化为7 - [(1 - 羟基 - 1 - 苯基) - 乙酰氨基] - 3 - 乙酰氧甲基 - Δ(3) - 头孢烯 - 4 - 羧酸，这是合成头孢孟多和头孢尼西的有用中间体。通过对相应的3'-官能化核进行直接酰化反应来合成这些头孢菌素时，也得到了类似的结果。在这些反应中，黏性节杆菌的合成性能高于来自大肠杆菌的PGA。
