WO2004062558A3 - Process for enzymatic synthesis of βετα-lactam antibiotics - Google Patents

Process for enzymatic synthesis of βετα-lactam antibiotics Download PDF

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Publication number
WO2004062558A3
WO2004062558A3 PCT/EP2004/000182 EP2004000182W WO2004062558A3 WO 2004062558 A3 WO2004062558 A3 WO 2004062558A3 EP 2004000182 W EP2004000182 W EP 2004000182W WO 2004062558 A3 WO2004062558 A3 WO 2004062558A3
Authority
WO
WIPO (PCT)
Prior art keywords
lactam antibiotics
βετα
enzymatic synthesis
lactam
reaction
Prior art date
Application number
PCT/EP2004/000182
Other languages
French (fr)
Other versions
WO2004062558A2 (en
Inventor
Paolo Linda
Lucia Gardossi
Micaela Toniutti
Original Assignee
Univ Degli Studi Trieste
Paolo Linda
Lucia Gardossi
Micaela Toniutti
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Univ Degli Studi Trieste, Paolo Linda, Lucia Gardossi, Micaela Toniutti filed Critical Univ Degli Studi Trieste
Publication of WO2004062558A2 publication Critical patent/WO2004062558A2/en
Publication of WO2004062558A3 publication Critical patent/WO2004062558A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P37/00—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin
    • C12P37/04—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin by acylation of the substituent in the 6 position
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
    • C12P35/04—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin by acylation of the substituent in the 7 position

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

The present invention describes a process for the preparation of β-lactam antibiotics, cephalexin and ampicillin, wherein the β-lactam nucleus is acylated with an acylating agent, D-phenylglycine, by means of a reaction biocatalyzed by a catalytic enzyme. The acylation reaction is carried out in solid phase in solvent free systems (water or organic solvents) for the dispersion of reagents and at controlled temperatures.
PCT/EP2004/000182 2003-01-14 2004-01-14 Process for enzymatic synthesis of βετα-lactam antibiotics WO2004062558A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI20030042 ITMI20030042A1 (en) 2003-01-14 2003-01-14 ENZYMATIC SYNTHESIS PROCESS OF B LACTAMIC ANTIBIOTICS.
ITMI2003A000042 2003-01-14

Publications (2)

Publication Number Publication Date
WO2004062558A2 WO2004062558A2 (en) 2004-07-29
WO2004062558A3 true WO2004062558A3 (en) 2005-06-09

Family

ID=32697277

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2004/000182 WO2004062558A2 (en) 2003-01-14 2004-01-14 Process for enzymatic synthesis of βετα-lactam antibiotics

Country Status (2)

Country Link
IT (1) ITMI20030042A1 (en)
WO (1) WO2004062558A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102851332A (en) * 2012-09-07 2013-01-02 石药集团中诺药业（石家庄）有限公司 Recovery method for D(-)phenylglycine in ampicillin mother liquid by using enzyme method

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011080739A2 (en) 2009-12-29 2011-07-07 Yeda Research And Development Co. Ltd. Synergistic antibiotic combinations and derivatives
CN106187795A (en) * 2016-07-05 2016-12-07 南京红杉生物科技有限公司 A kind of synthetic method of D Phenylglycine methyl ester

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0730035A1 (en) * 1995-02-28 1996-09-04 ACS DOBFAR S.p.A. Improved enzymatic process for producing penicillins and cephalosporins
WO1997004086A1 (en) * 1995-07-18 1997-02-06 Gist-Brocades B.V. An improved immobilized penicillin g acylase
WO1998020120A1 (en) * 1996-11-05 1998-05-14 Bristol-Myers Squibb Company Mutant penicillin g acylases
WO1999001566A1 (en) * 1997-07-03 1999-01-14 Dsm N.V. PREPARATION OF ENZYME WITH REDUCED β-LACTAMASE ACTIVITY
US6218138B1 (en) * 1998-05-26 2001-04-17 Unifar Kimya Sanayi Ve Ticaret A.S. Synthesis of beta-lactam antibiotics with immobilized penicillin amidase

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0730035A1 (en) * 1995-02-28 1996-09-04 ACS DOBFAR S.p.A. Improved enzymatic process for producing penicillins and cephalosporins
WO1997004086A1 (en) * 1995-07-18 1997-02-06 Gist-Brocades B.V. An improved immobilized penicillin g acylase
WO1998020120A1 (en) * 1996-11-05 1998-05-14 Bristol-Myers Squibb Company Mutant penicillin g acylases
WO1999001566A1 (en) * 1997-07-03 1999-01-14 Dsm N.V. PREPARATION OF ENZYME WITH REDUCED β-LACTAMASE ACTIVITY
US6218138B1 (en) * 1998-05-26 2001-04-17 Unifar Kimya Sanayi Ve Ticaret A.S. Synthesis of beta-lactam antibiotics with immobilized penicillin amidase

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ARROYO M ET AL: "Biotechnological applications of penicillin acylases: State-of-the-art.", APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, vol. 60, no. 5, January 2003 (2003-01-01), pages 507 - 514, XP002280220, ISSN: 0175-7598 *
BELL GEORGE ET AL: "Biocatalyst behaviour in low-water systems", TRENDS IN BIOTECHNOLOGY, vol. 13, no. 11, 1995, pages 468 - 473, XP002280222, ISSN: 0167-7799 *
FERNANDEZ-LAFUENTE R ET AL: "The presence of methanol exerts a strong and complex modulation of the synthesis of different antibiotics by immobilized penicillin G acylase", ENZYME AND MICROBIAL TECHNOLOGY, vol. 23, no. 5, October 1998 (1998-10-01), pages 305 - 310, XP002280221, ISSN: 0141-0229 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102851332A (en) * 2012-09-07 2013-01-02 石药集团中诺药业（石家庄）有限公司 Recovery method for D(-)phenylglycine in ampicillin mother liquid by using enzyme method

Also Published As

Publication number Publication date
ITMI20030042A1 (en) 2004-07-15
WO2004062558A2 (en) 2004-07-29

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