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A8398 Sigma

7-Aminodesacetoxycephalosporanic acid

Synonym: 7-ADCA

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Description

Application

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7-Aminodesacetoxycephalosporanic acid is used in the synthesis of cephalosporins and for bioconversion studies 1.

7-Aminodesacetoxycephalosporanic acid is used in the synthesis of cephalosporins.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Biochem/physiol Actions

7-ADCA is produced from penicillin G made by Penicillium chrysogenum involving several polluting chemical steps followed by enzymatic deacylation using penicillin acylase 2.

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.



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7-<WBR>Aminodesacetoxycephalosporanic acid

European Pharmacopoeia (EP) Reference Standard

ammonium sulfate suspension, ≥10 units/mg protein (E1%/280)

5-10 units/mg protein

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
36
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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1. Altering the Substrate Specificity of Cephalosporin Acylase by Directed Evolution of the β-Subunit. Linda G. Otten, Charles F. Sio, et al. J. Biol. Chem. 277, 42121-42127, (2002)

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2. Mutational analysis of a key residue in the substrate specificity of a cephalosporin acylase. Linda G. Otten, Charles F. Sio, et al. ChemBioChem. 6, 820-825, (2004)

Modeling of the enzymatic kinetic synthesis of cephalexin--influence of substrate concentration and temperature. Schroën CG, Nierstrasz VA, Moody HM, et al. Biotechnol. Bioeng. 73(3), 171-8, (2001)

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Kinetics of enzyme acylation and deacylation in the penicillin acylase-catalyzed synthesis of beta-lactam antibiotics. Alkema WB, de Vries E, Floris R, et al. Eur. J. Biochem. 270(18), 3675-83, (2003)

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Integrated reactor concepts for the enzymatic kinetic synthesis of cephalexin. Schroën CG, Nierstrasz VA, Bosma R, et al. Biotechnol. Bioeng. 80(2), 144-55, (2002)

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A two-step, one-pot enzymatic synthesis of cephalexin from D-phenylglycine nitrile. Wegman MA, van Langen LM, van Rantwijk F, et al. Biotechnol. Bioeng. 79(3), 356-61, (2002)

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Advantages of using non-isothermal bioreactors for the enzymatic synthesis of antibiotics: the penicillin G acylase as enzyme model. Travascio P, Zito E, De Maio A, et al. Biotechnol. Bioeng. 79(3), 334-46, (2002)

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[Role of biocatalysis in the creation and improvement of production of beta-lactam antibiotics in Russia]. Nys PS and Bartoshevich IuE Antibiot. Khimioter. 39(8), 3-14, (1994)

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Anaerobic stabilization and conversion of transformed intermediates of antibiotic pharmaceutical effluent in a fluidized bed reactor. Tamijevendane S, Saravanane R, Rajesh R, et al. J. Environ. Sci. Eng. 53(3), 231-6, (2011)

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Effect of loading rate and HRT on the removal of cephalosporin and their intermediates during the operation of a membrane bioreactor treating pharmaceutical wastewater. Saravanane R and Sundararaman S Environ. Technol. 30(10), 1016-22, (2009)

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Enzymatic preparation of cefaclor with immobilized penicillin acylase. Zhang YW and Wei DZ Prep Biochem Biotechnol. 38(2), 129-38, (2008)

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[Enzymatic synthesis of cephradine]. Cui F, Shi J, and Bai X Wei Sheng Wu Xue Bao 38(4), 300-3, (1998)

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[Hydrolase from Xanthomonas rubrilineans for synthesis of cefalexin]. Ivankin AN and Nekliudov AD Prikl. Biokhim. Mikrobiol. 36(3), 303-6, (2000)

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Equilibrium position, kinetics, and reactor concepts for the adipyl-7-ADCA-hydrolysis process. Schroën CG, VandeWiel S, Kroon PJ, et al. Biotechnol. Bioeng. 70(6), 654-61, (2000)

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Production of cephalosporin intermediates by feeding adipic acid to recombinant Penicillium chrysogenum strains expressing ring expansion activity. Crawford L, Stepan AM, McAda PC, et al. Biotechnology. (N.Y.) 13(1), 58-62, (1995)

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Continuous cultivations of a Penicillium chrysogenum strain expressing the expandase gene from Streptomyces clavuligerus: Kinetics of adipoyl-7-aminodeacetoxycephalosporanic acid and byproduct formations. Robin J, Bruheim P, Nielsen ML, et al. Biotechnol. Bioeng. 83(3), 353-60, (2003)

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Environmentally safe production of 7-aminodeacetoxycephalosporanic acid (7-ADCA) using recombinant strains of Acremonium chrysogenum. Velasco J, Luis Adrio J, Angel Moreno M, et al. Nat. Biotechnol. 18(8), 857-61, (2000)

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Continuous cultivations of a Penicillium chrysogenum strain expressing the expandase gene from Streptomyces clavuligerus: Growth yields and morphological characterization. Robin J, Lettier G, McIntyre M, et al. Biotechnol. Bioeng. 83(3), 361-8, (2003)

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Process design for enzymatic adipyl-7-ADCA hydrolysis. Schroën CG, Nierstrasz VA, Bosma R, et al. Biotechnol. Prog. 18(4), 745-51, (2002)

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Penicillin acylase-catalyzed synthesis of beta-lactam antibiotics in highly condensed aqueous systems: beneficial impact of kinetic substrate supersaturation. Youshko MI, Moody HM, Bukhanov AL, et al. Biotechnol. Bioeng. 85(3), 323-9, (2004)

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Analysis of a substrate specificity switch residue of cephalosporin acylase. Sio CF, Otten LG, Cool RH, et al. Biochem. Biophys. Res. Commun. 312(3), 755-60, (2003)

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Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase. Dubus A, Lloyd MD, Lee HJ, et al. Cell. Mol. Life Sci. 58(5-6), 835-43, (2001)

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Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions. Youshko MI, Chilov GG, Shcherbakova TA, et al. Biochim. Biophys. Acta 1599(1-2), 134-40, (2002)

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Enzymatic production of cephalexin. Maladkar NK Enzyme Microb. Technol. 16(8), 715-8, (1994)

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Enzyme reaction engineering: effect of methanol on the synthesis of antibiotics catalyzed by immobilized penicillin G acylase under isothermal and non-isothermal conditions. Travascio P, Zito E, Portaccio M, et al. Biotechnol. Prog. 18(5), 975-85, (2002)

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Enhanced enzymatic synthesis of a semi-synthetic cephalosprin, cefaclor, with in situ product removal. Yang L and Wei DZ Biotechnol. Lett. 25(14), 1195-8, (2003)

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Enzymatic 7-ADCA: I said it couldn't be done. Demain A Biotechnology. (N.Y.) 13(1), 23-4, (1995)

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