Enzymatic acylation of 3-hydroxymethyl cephalosporins

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing compound having a 1-thia-5-aza-bicyclo

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435 48, 435 49, 435 50, 435 51, 435196, 435197, 435198, 435839, 435911, 435917, C12P 3504, C12P 3506, C12N 920

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055124542

ABSTRACT:
O-acylated cephalosporins are produced by reacting 3-hydroxymethylcephalosporins with an acyl donor containing at least three carbon atoms and an enzyme which is a Rodosporidium toruloides esterase, a wheat germ lipase, an Aspergillus niger lipase, an orange peel acetylesterase or a Bacillus subtilis esterase. A preferred enzyme is the esterase from Rodosporidium toruloides ATCC 10657. The enzyme can be used while in whole cells or in soluble or inmobilized form.

REFERENCES:
patent: 3202656 (1965-08-01), Abraham et al.
patent: 3239394 (1966-03-01), Walton
patent: 3304310 (1967-02-01), Hari et al.
patent: 3436310 (1969-04-01), Arnold et al.
patent: 3522248 (1970-07-01), Voser
patent: 3532694 (1970-10-01), Somerfield et al.
patent: 3573296 (1971-03-01), Johnson et al.
patent: 3641018 (1972-02-01), Hayes et al.
patent: 3821208 (1974-06-01), Stables et al.
patent: 3853863 (1974-12-01), Jackson et al.
patent: 3980644 (1976-09-01), Lunn
patent: 4414328 (1983-11-01), Imanaka
patent: 4459405 (1984-07-01), Hall
patent: 4472503 (1984-09-01), Matsuo et al.
patent: 4533632 (1985-08-01), Smith et al.
patent: 4584371 (1986-04-01), Timko
patent: 4861716 (1989-08-01), Marcuse et al.
patent: 4892822 (1990-01-01), Abramowicz et al.
patent: 5220063 (1993-06-01), Tafesh et al.
patent: 5221739 (1993-06-01), Wildfeuer
patent: 5229274 (1993-07-01), Crawford et al.
Ogata, et al, "Preparation of Water-insoluble, Enzymatically Active Derivatives of Subtilisin Type Novo by Cross-linking with Glutaraldehyde," Biochim. Biophys. Acta, 159, 403-405 (1968).
Singer, "On The Mechanism of Enzyme Inhibition by Sulfhydryl Reagents," Journal of Biological Chemistry, 174, 11-21 (1948).
Malcata, et al, "Use of a Lipase Immobilized in a Membrane Reactor to Hydrolyze the Glycerides of Butteroil," Biotechnology and Bioengineering, 38, 853-868 (1991).
Newton, et al, "Cephalosporin C, a New Antibiotic Containing Sulphur and D-.alpha.-Aminoadipic Acid," Nature, 175, 548 (1955).
Andrisano, et al, "Extraction of Cephalsporic C from Fermentation Broths via Lipophilic Intermediates and the Production of 7-Aminocephalosporanic Acid (7-ACA)," J. Appl. Chem. Biotechnol., 26, 459-468 (1976).
Moris, et al, "A Useful and Versatile Procedure for the Acylation of Nucleosides through an Enzymatic Reaction," J. Org. Chem., 58, 653-660 (1993).
Gotor, et al, "Enantioselective Acylation of Amino Alcohols by Porcine Pancreatic Lipase," J. Chem. Soc., Chem. Commun., 957-958 (1988).
Nageo, et al, "Synthesis of O-Acyl-L-Homoserine by Lipase," JAOCS, 66(5), 710-713 (1989).
Akita, et al, "Enantioselective Acetylation of an .alpha.-Hydroxy Ester by Using Ether-Linked Lipid-Lipase Aggregates in Organic Solvents," Chem. Pharm. Bull., 41(1), 16-20 (1993).
Adelhorst, et al, "Enzyme Catalysed Preparation of 6-O-Acylglucopyranosides," Synthesis, 112-115 (1990).
Nicolosi, et al, "Lipase-catalyzed Regioselective Protection of Hydroxy Groups in Aromatic Dihydroxyaldehydes and Ketones," Tetrahedron, 49, 3143-3148 (1993).
Panza, et al, "Selective Lipase-catalyzed Acylation of 4,5-O-Benzylidene-D-Glucopyranosides to Synthetically Useful Esters," Tetrahedron: Asymmetry, 4(5), 931-932 (1993).
Kato, et al, "Enzymatic synthesis of Amoxicillin by the Cell-Bound .alpha.-Amino Acid Ester Hydrolase of Xanthomonas citri," Agric. Biol. Chem., 44(4), 821-825 (1980).
Jeffrey, et al, "Deacetylcephalosporin C," Biochemical Journal, 81, 591-596 (1961).

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