Title:
AN ENZYMATIC PROCESS FOR PREPARING BETA-LACTAMS
Document Type and Number:
WIPO Patent Application WO2004020650
Kind Code:
A3
Abstract:
An enzymatic process under kinetical control for preparing b-lactams, by coupling the 7-amino group of a cephalosporin nucleus with the carboxylic function of an acetic acid derivative consisting of a residue with p-electrons, a short spacer and a carboxylic function activated as methyl- or ethylester. The process comprises using a penicillin amidase or a-amino acid esterase as free enzyme or in any suitable immobilised form; applying at least 100 mmol/l cephalosporin nucleus as long as it is soluble, otherwise 50 - 100 % of its maximum solubility is charged, applying the acetic acid activated as ester in a 1 - 3 fold molar ratio, and adjusting the pH to 6.0 - 8.0 and the temperature to 0 - 30 DEG C.
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Inventors:
GIESECKE ULRICH EBERHARD (DE)
Application Number:
PCT/EP2003/009659
Publication Date:
November 18, 2004
Filing Date:
August 29, 2003
Export Citation:
Assignee:
BIOFERMA MURCIA S A (ES)
GIESECKE ULRICH EBERHARD (DE)
GIESECKE ULRICH EBERHARD (DE)
International Classes:
C12P35/00; C12P35/02; C12P35/04; (IPC1-7): C12P35/04; C12P35/00; C12P35/02
Domestic Patent References:
| WO1999020786A1 | 1999-04-29 | |||
| WO1992001061A1 | 1992-01-23 | |||
| WO1996002663A1 | 1996-02-01 |
Foreign References:
| US3853705A | 1974-12-10 | |||
| US3945888A | 1976-03-23 | |||
| EP0458932A1 | 1991-12-04 | |||
| US4340672A | 1982-07-20 |
Other References:
BUDAVARI S ET AL: "The Merck Index", 1996, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002285534
SHAW S-Y ET AL: "Enzymatic synthesis of cephalothin by penicillin G acylase.", ENZYME AND MICROBIAL TECHNOLOGY, vol. 26, no. 2-4, February 2000 (2000-02-01), pages 142 - 151, XP002233338, ISSN: 0141-0229
FERNANDEZ-LAFUENTE R ET AL: "Synthesis of antibiotics (cephaloglycin) catalyzed by penicillin G acylase: Evaluation and optimization of different synthetic approaches", ENZYME AND MICROBIAL TECHNOLOGY, vol. 19, no. 1, July 1996 (1996-07-01), pages 9 - 14, XP001098845
BRUGGINK A ET AL.: "Penicillin acylase in the industrial production of beta-lactam antibiotics", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 2, no. 2, March 1998 (1998-03-01), pages 128 - 133, XP002233341
KASCHE V: "Mechanism and yields in enzyme-catalyzed equilibrium and kinetically controlled synthesis of beta-lactam antibiotics, peptides and other condensation products", ENZYME AND MICROBIAL TECHNOLOGY, vol. 8, no. 1, 1986, pages 4 - 16, XP008014254, ISSN: 0141-0229
FERNANDEZ-LAFUENTE R ET AL: "Industiral synthesis of semi-synthetic beta-lactam antibiotics: recent develoments in enzyme biocatalysis for improved and MORE sustainable processes", CURRENT MEDICINAL CHEMISTRY. ANTI-INFECTIVE AGENTS, vol. 1, no. 4, October 2002 (2002-10-01), pages 375 - 387, XP008024939, ISSN: 1568-0118
BUDAVARI S ET AL: "The Merck Index", 1996, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002285535
KUROCHKINA V B ET AL: "Kinetic and thermodynamic approach to design of processes for enzymatic synthesis of beta lactams", BIOCATALYSIS AND BIOTRANSFORMATION, vol. 20, no. 1, 2002, pages 35 - 41, XP008029122
JUSTIZ O H ET AL: "One-pot chemoenzymatic synthesis of 3'-functionalized cephalosporines ( cefazolin ) by three consecutive biotransformations in fully aqueous medium", JOURNAL OF ORGANIC CHEMISTRY, vol. 62, no. 26, 26 December 1997 (1997-12-26), pages 9099 - 9106, XP002233339
SHIMIZU M ET AL: "Purification and properties of penicillin acylase from Kluyvera citrophila", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 39, no. 8, 1975, pages 1655 - 1661, XP002262195, ISSN: 0002-1369
BUDAVARI S ET AL: "The Merck Index", 1996, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002285536
WON J I ET AL: "The effect of 2-mercapto-5-methyl-1,3,4-thiadiazole on enzymatic synthesis of cefazolin", APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, vol. 69, no. 1, January 1998 (1998-01-01), pages 1 - 9, XP001105929, ISSN: 0273-2289
NYS P S ET AL: "Methodological approach to development of enzymatic technologies for semisynthetic betalactam antibiotic production", APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, vol. 88, no. 1-3, 2000, pages 221 - 229, XP009028860, ISSN: 0273-2289
KOSTADINOV M ET AL: "New tetrazole-1-acetic acid esters for enzymatic synthesis of cefazolin", APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, vol. 33, no. 3, June 1992 (1992-06-01), pages 178 - 182, XP008014282, ISSN: 0273-2289
PARK C B ET AL: "Penicillin acylase-catalyzed synthesis of cefazolin in water-solvent mixtures: enhancement effect of ethyl acetate and carbon tetrachloride on the synthetic yield", JOURNAL OF MOLECULAR CATALYSIS. B, ENZYMATIC, vol. 9, no. 4-6, 21 April 2000 (2000-04-21), pages 275 - 281, XP000989461, ISSN: 1381-1177
BUDAVARI S ET AL: "The Merck Index", 1996, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002285537
PATENT ABSTRACTS OF JAPAN vol. 0040, no. 26 (C - 001) 6 March 1980 (1980-03-06)
BUDAVARI S ET AL: "The Merck index", 1996, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002285538
DATABASE WPI Section Ch Week 197813, Derwent World Patents Index; Class B02, AN 1978-23858A, XP002285540
KONECNY J ET AL: "Kinetics and mechanism of acyl transfer by penicillin acylases", BIOTECHNOLOGY AND BIOENGINEERING, vol. 25, no. 2, 1983, pages 451 - 468, XP002285532, ISSN: 0006-3592
KONECNY J ET AL: "Kinetics and mechanism of acyl transfer by penicillin acylases EC-3.5.1.11", BIOTECHNOLOGY LETTERS, vol. 3, no. 9, 1981, pages 507 - 512, XP008031897, ISSN: 0141-5492
SHAW S-Y ET AL: "Enzymatic synthesis of cephalothin by penicillin G acylase.", ENZYME AND MICROBIAL TECHNOLOGY, vol. 26, no. 2-4, February 2000 (2000-02-01), pages 142 - 151, XP002233338, ISSN: 0141-0229
FERNANDEZ-LAFUENTE R ET AL: "Synthesis of antibiotics (cephaloglycin) catalyzed by penicillin G acylase: Evaluation and optimization of different synthetic approaches", ENZYME AND MICROBIAL TECHNOLOGY, vol. 19, no. 1, July 1996 (1996-07-01), pages 9 - 14, XP001098845
BRUGGINK A ET AL.: "Penicillin acylase in the industrial production of beta-lactam antibiotics", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 2, no. 2, March 1998 (1998-03-01), pages 128 - 133, XP002233341
KASCHE V: "Mechanism and yields in enzyme-catalyzed equilibrium and kinetically controlled synthesis of beta-lactam antibiotics, peptides and other condensation products", ENZYME AND MICROBIAL TECHNOLOGY, vol. 8, no. 1, 1986, pages 4 - 16, XP008014254, ISSN: 0141-0229
FERNANDEZ-LAFUENTE R ET AL: "Industiral synthesis of semi-synthetic beta-lactam antibiotics: recent develoments in enzyme biocatalysis for improved and MORE sustainable processes", CURRENT MEDICINAL CHEMISTRY. ANTI-INFECTIVE AGENTS, vol. 1, no. 4, October 2002 (2002-10-01), pages 375 - 387, XP008024939, ISSN: 1568-0118
BUDAVARI S ET AL: "The Merck Index", 1996, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002285535
KUROCHKINA V B ET AL: "Kinetic and thermodynamic approach to design of processes for enzymatic synthesis of beta lactams", BIOCATALYSIS AND BIOTRANSFORMATION, vol. 20, no. 1, 2002, pages 35 - 41, XP008029122
JUSTIZ O H ET AL: "One-pot chemoenzymatic synthesis of 3'-functionalized cephalosporines ( cefazolin ) by three consecutive biotransformations in fully aqueous medium", JOURNAL OF ORGANIC CHEMISTRY, vol. 62, no. 26, 26 December 1997 (1997-12-26), pages 9099 - 9106, XP002233339
SHIMIZU M ET AL: "Purification and properties of penicillin acylase from Kluyvera citrophila", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 39, no. 8, 1975, pages 1655 - 1661, XP002262195, ISSN: 0002-1369
BUDAVARI S ET AL: "The Merck Index", 1996, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002285536
WON J I ET AL: "The effect of 2-mercapto-5-methyl-1,3,4-thiadiazole on enzymatic synthesis of cefazolin", APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, vol. 69, no. 1, January 1998 (1998-01-01), pages 1 - 9, XP001105929, ISSN: 0273-2289
NYS P S ET AL: "Methodological approach to development of enzymatic technologies for semisynthetic betalactam antibiotic production", APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, vol. 88, no. 1-3, 2000, pages 221 - 229, XP009028860, ISSN: 0273-2289
KOSTADINOV M ET AL: "New tetrazole-1-acetic acid esters for enzymatic synthesis of cefazolin", APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, vol. 33, no. 3, June 1992 (1992-06-01), pages 178 - 182, XP008014282, ISSN: 0273-2289
PARK C B ET AL: "Penicillin acylase-catalyzed synthesis of cefazolin in water-solvent mixtures: enhancement effect of ethyl acetate and carbon tetrachloride on the synthetic yield", JOURNAL OF MOLECULAR CATALYSIS. B, ENZYMATIC, vol. 9, no. 4-6, 21 April 2000 (2000-04-21), pages 275 - 281, XP000989461, ISSN: 1381-1177
BUDAVARI S ET AL: "The Merck Index", 1996, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002285537
PATENT ABSTRACTS OF JAPAN vol. 0040, no. 26 (C - 001) 6 March 1980 (1980-03-06)
BUDAVARI S ET AL: "The Merck index", 1996, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002285538
DATABASE WPI Section Ch Week 197813, Derwent World Patents Index; Class B02, AN 1978-23858A, XP002285540
KONECNY J ET AL: "Kinetics and mechanism of acyl transfer by penicillin acylases", BIOTECHNOLOGY AND BIOENGINEERING, vol. 25, no. 2, 1983, pages 451 - 468, XP002285532, ISSN: 0006-3592
KONECNY J ET AL: "Kinetics and mechanism of acyl transfer by penicillin acylases EC-3.5.1.11", BIOTECHNOLOGY LETTERS, vol. 3, no. 9, 1981, pages 507 - 512, XP008031897, ISSN: 0141-5492
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