Cross penicillin acylase

Wu et al. [183] studied the reversible hydrolysis of penicillin G into 6-aminopeni-cillanic acid (6-APA) and phenylacetic acid (PAA) in a chromatographic reactor. E. coli cells containing penicillin acylase (the catalyst) were immobilized by entrapment into gelatine and further cross-linking with glutaraldehyde. The ad-... 

Cao, L., van Rantwijk, F. and Sheldon, R.A. (2000) Cross-linked enzyme aggregates a simple and effective method for the immobilization of penicillin acylase. Org. Lett., 2, 1361. 

Cao, L., van Langen, L.M., Rantwijk, R, and Sheldon, R.A. 2001. Cross-linked aggregates of penicillin acylase Robust catalysts for the synthesis of (3-lactam antibiotics. Journal of Molecular Catalysis B Enzymatic, 11 665-70. 

Penicillin acylase Enzyme E. coli Entrapment + cross-linking [40]... 

Dixon M, Webb EC (1979) Enzymes, 3rd edn. Academic Press, New York, 1116 pp Eisenthal R, Cornish-Bowden A (1974) The direct linear plot. A new graphical procedure for estimating enzyme kinetic parameters. Biochem J 139(3) 715-720 Ertan H, Kazan D, Erarslan (1997) Cross-hnked stabilization of Escherichia coli penicilhn G acy-lase against pH by dextran-dialdedhyde polymers. Biotechnol Tech 11 225-229 Ferreira JS, Straathof AJJ, Franco TT et al. (2004) Activity and stability of immobilized penicillin acylase at low pH values. J Mol Catal B Enzym 27 29-35 Guranda DT, Volovik TS, Svedas VK (2004) pH stability of penicillin acylase from Escherichia coli. Biochemistry (Moscow) 69(12) 1700-1705... 

Cao L, van Rantwijk F, Sheldon R (2000) Cross-linked enzyme aggregates a simple and effective method for the immobilization of penicillin acylase. Oig Lett 2 1361-1364 Cao L, van Langen F, van Rantwijk F et til. (2(X)1) Cross-linked aggregates of peniciUin acylase robust catalysts for the synthesis of (3-lactam antibiotics. J Mol Catal B Enzym 11 665-670 Cao L, van Langen L, Sheldon R (2003) ImmobDised enzymes carrier-bound or carrier-free Cuir Opin Biotechnol 14 1-8... 

Rev. 42 (2013) 6213-6222. (d) L. Cao, F.v. Rantwijk, R.A. Sheldon, Cross-linked enzyme aggregates a simple and effective method for the immobilization of penicillin acylase, Org. Lett. 2 (2000) 1361-1364. (e) T. Matsuda, K. Nakayama, T. Abe, M. Mukouyama, Stabilization of pyruvate decarboxylase under pressurized carbon dioxide and water biphasic system, Biocatal. Bio-trans. 28 (2010) 167-171. (f)T. Matsuda, R. Marukado, M. Mukouyama, . Harada, K. Nakamura, Asymmetric reduction of ketones by Geotrichum candidum immobilization and application to reactions using supercritical carbon dioxide. Tetrahedron Asymm. 19 (2008) 2272-2275. 

En2yme techniques are primarily developed for commercial reasons, and so information about immobilisation and process conditions is usually Limited. A commercially available immobilised penicillin V acylase is made by glutaraldehyde cross-linking of a cell homogenate. It can be used ia batch stirred tank or recycled packed-bed reactors with typical operating parameters as iadicated ia Table 2 (38). Further development may lead to the creation of acylases and processes that can also be used for attaching side chains by ensymatic synthesis. 

ChiroCLEC -EC is cross-linked crystals of penicillin-G acylase and is available from Altus Biologies, Inc., Cambridge, MA. 

An enzyme-labile so-called safety catch linker 452 was used successfully in various palladium-catalyzed cross-coupling reactions [592]. The linker 452, which releases a hydroxy or an amino functionality on enzymatic cleavage of its phenylacetamide moiety and subsequent rapid lactam formation, was attached to a soluble POE 6000 (polyethylene oxide) polymer and its free phenylacetic acid moiety was transformed to an m-iodobenzyl ester. The thus immobilized m-iodobenzyl alcohol was Heck-coupled with tert-butyl acrylate, and the coupling product 453 was cleaved off the solid support with penicillin G acylase under very mild conditions (pH 7, 37°C) (Scheme 8.84). 

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