Title:
AN ENZYMATIC PROCESS FOR THE SYNTHESIS OF ORGANO-FLUORINE COMPOUNDS
Document Type and Number:
WIPO Patent Application WO2003020945
Kind Code:
A3
Abstract:
There is described a process for the synthesis of a fluoronucleoside compound, said process comprising mixing a substrate and an enzyme from Streptomyces cattelya as catalyst. The process may be used to produce an 18F labelled fluoronucleoside compound. There is also described an enzyme derived from Streptomyces cattelya which has the capacity to catalyse the synthesis of a fluoronucleoside compound. (Formula I).
Inventors:
O'HAGAN DAVID (GB)
SCHAFFRATH CHRISTOPH (DE)
SCHAFFRATH CHRISTOPH (DE)
Application Number:
PCT/GB2002/004032
Publication Date:
September 25, 2003
Filing Date:
September 05, 2002
Export Citation:
Assignee:
UNIV ST ANDREWS (GB)
O'HAGAN DAVID (GB)
SCHAFFRATH CHRISTOPH (DE)
O'HAGAN DAVID (GB)
SCHAFFRATH CHRISTOPH (DE)
International Classes:
A61K51/04; C12N9/00; C12P19/40; (IPC1-7): C12P19/40; C12P7/54; C12N9/00; C12N9/10; A61K51/04
Other References:
MOSS S J ET AL: "Fluoroacetaldehyde: A precursor of both fluoroacetate and 4-fluorothreonine in Streptomyces cattleya", CHEMICAL COMMUNICATIONS 21 NOV 2000 UNITED KINGDOM, vol. 6, no. 22, 21 November 2000 (2000-11-21), pages 2281 - 2282, XP002236667, ISSN: 1359-7345
SANADA M ET AL: "BIOSYNTHESIS OF FLUOROTHREONINE AND FLUOROACETIC-ACID BY THE THIENAMYCIN PRODUCER STREPTOMYCES-CATTLEYA", JOURNAL OF ANTIBIOTICS (TOKYO), vol. 39, no. 2, 1986, pages 259 - 265, XP002236536, ISSN: 0021-8820
TAMURA TAKASHI ET AL: "Synthesis of fluoroacetate from fluoride, glycerol and beta-hydroxypyruvate by Streptomyces cattleya.", JOURNAL OF BACTERIOLOGY, vol. 177, no. 9, 1995, pages 2265 - 2269, XP002236537, ISSN: 0021-9193
REID KAREN A ET AL: "Biosynthesis of fluorinated secondary metabolites by Streptomyces cattleya.", MICROBIOLOGY (READING), vol. 141, no. 6, 1995, pages 1385 - 1393, XP008015651, ISSN: 1350-0872
O'HAGAN DAVID ET AL: "Biochemistry: biosynthesis of an organofluorine molecule.", NATURE. ENGLAND 21 MAR 2002, vol. 416, no. 6878, 21 March 2002 (2002-03-21), pages 279, XP002236535, ISSN: 0028-0836
SCHAFFRATH CHRISTOPH ET AL: "Cell-free biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya.", ANGEWANDTE CHEMIE (INTERNATIONAL ED. IN ENGLISH) GERMANY 18 OCT 2002, vol. 41, no. 20, 18 October 2002 (2002-10-18), pages 3913 - 3915, XP002236538, ISSN: 0570-0833
O'HAGAN DAVID ET AL: "Assay for the enantiomeric analysis of (2H1)-fluoroacetic acid: Insight into the stereochemical course of fluorination during fluorometabolite biosynthesis in Streptomyces cattleya.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 2, 15 January 2003 (2003-01-15), pages 379 - 387, XP002236539, ISSN: 0002-7863
HAMILTON J T G ET AL: "Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. Glycine and pyruvate as precursors", CHEMICAL COMMUNICATIONS 1997 UNITED KINGDOM, vol. 2, no. 8, 1997, pages 797 - 798, XP002236666, ISSN: 1359-7345
SAVARESE T M ET AL: "5' DEOXY-5'-METHYLTHIOADENOSINE PHOSPHORYLASE 3. ROLE OF THE ENZYME IN THE METABOLISM AND ACTION OF 5' HALOGENATED ADENOSINE ANALOGS", BIOCHEMICAL PHARMACOLOGY, vol. 34, no. 3, 1985, pages 361 - 368, XP008015842, ISSN: 0006-2952
ZECHEL D L ET AL: "Enzymatic synthesis of carbon-fluorine bonds.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. UNITED STATES 9 MAY 2001, vol. 123, no. 18, 9 May 2001 (2001-05-09), pages 4350 - 4351, XP002236668, ISSN: 0002-7863
LEHEL SZ ET AL: "Synthesis of 5'-deoxy-5'-[F]fluoro-adenosine by radiofluorination of 5'-deoxy-5'-haloadenosine derivatives", JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY 2000 HUNGARY, vol. 245, no. 2, 2000, pages 399 - 401, XP008019765, ISSN: 0236-5731
CHERIF ABDALLAH ET AL: "Radiosynthesis and biodistribution studies of (F-18)fluoroadenosine and (I-131)-5-iodo-2'-O-methyl-uridine, for the assessment of tumor proliferation rate.", PHARMACEUTICAL RESEARCH (NEW YORK), vol. 12, no. 9 SUPPL., 1995, Annual Meeting of the American Association of Pharmaceutical Scientists;Miami Beach, Florida, USA; November 5-9, 1995, pages S128, XP008019780, ISSN: 0724-8741
ALAUDDIN M M ET AL: "Evaluation of 9-[(3-F-fluoro-1-hydroxy-2-propoxy)methyl]guanine ([F]-FHPG) in vitro and in vivo as a probe for PET imaging of gene incorporation and expression in tumors - Initial evaluation with PET with the radiolabeled glucose analogue 2-(F-18)fluoro-2-deoxy-d-glucose", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US, vol. 26, no. 4, May 1999 (1999-05-01), pages 371 - 376, XP004167069, ISSN: 0969-8051
VARAGNOLO L ET AL: "F-labeled radiopharmaceuticals for PET in oncology, excluding FDG", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US, vol. 27, no. 2, February 2000 (2000-02-01), pages 103 - 112, XP004196577, ISSN: 0969-8051
SANADA M ET AL: "BIOSYNTHESIS OF FLUOROTHREONINE AND FLUOROACETIC-ACID BY THE THIENAMYCIN PRODUCER STREPTOMYCES-CATTLEYA", JOURNAL OF ANTIBIOTICS (TOKYO), vol. 39, no. 2, 1986, pages 259 - 265, XP002236536, ISSN: 0021-8820
TAMURA TAKASHI ET AL: "Synthesis of fluoroacetate from fluoride, glycerol and beta-hydroxypyruvate by Streptomyces cattleya.", JOURNAL OF BACTERIOLOGY, vol. 177, no. 9, 1995, pages 2265 - 2269, XP002236537, ISSN: 0021-9193
REID KAREN A ET AL: "Biosynthesis of fluorinated secondary metabolites by Streptomyces cattleya.", MICROBIOLOGY (READING), vol. 141, no. 6, 1995, pages 1385 - 1393, XP008015651, ISSN: 1350-0872
O'HAGAN DAVID ET AL: "Biochemistry: biosynthesis of an organofluorine molecule.", NATURE. ENGLAND 21 MAR 2002, vol. 416, no. 6878, 21 March 2002 (2002-03-21), pages 279, XP002236535, ISSN: 0028-0836
SCHAFFRATH CHRISTOPH ET AL: "Cell-free biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya.", ANGEWANDTE CHEMIE (INTERNATIONAL ED. IN ENGLISH) GERMANY 18 OCT 2002, vol. 41, no. 20, 18 October 2002 (2002-10-18), pages 3913 - 3915, XP002236538, ISSN: 0570-0833
O'HAGAN DAVID ET AL: "Assay for the enantiomeric analysis of (2H1)-fluoroacetic acid: Insight into the stereochemical course of fluorination during fluorometabolite biosynthesis in Streptomyces cattleya.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 2, 15 January 2003 (2003-01-15), pages 379 - 387, XP002236539, ISSN: 0002-7863
HAMILTON J T G ET AL: "Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. Glycine and pyruvate as precursors", CHEMICAL COMMUNICATIONS 1997 UNITED KINGDOM, vol. 2, no. 8, 1997, pages 797 - 798, XP002236666, ISSN: 1359-7345
SAVARESE T M ET AL: "5' DEOXY-5'-METHYLTHIOADENOSINE PHOSPHORYLASE 3. ROLE OF THE ENZYME IN THE METABOLISM AND ACTION OF 5' HALOGENATED ADENOSINE ANALOGS", BIOCHEMICAL PHARMACOLOGY, vol. 34, no. 3, 1985, pages 361 - 368, XP008015842, ISSN: 0006-2952
ZECHEL D L ET AL: "Enzymatic synthesis of carbon-fluorine bonds.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. UNITED STATES 9 MAY 2001, vol. 123, no. 18, 9 May 2001 (2001-05-09), pages 4350 - 4351, XP002236668, ISSN: 0002-7863
LEHEL SZ ET AL: "Synthesis of 5'-deoxy-5'-[F]fluoro-adenosine by radiofluorination of 5'-deoxy-5'-haloadenosine derivatives", JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY 2000 HUNGARY, vol. 245, no. 2, 2000, pages 399 - 401, XP008019765, ISSN: 0236-5731
CHERIF ABDALLAH ET AL: "Radiosynthesis and biodistribution studies of (F-18)fluoroadenosine and (I-131)-5-iodo-2'-O-methyl-uridine, for the assessment of tumor proliferation rate.", PHARMACEUTICAL RESEARCH (NEW YORK), vol. 12, no. 9 SUPPL., 1995, Annual Meeting of the American Association of Pharmaceutical Scientists;Miami Beach, Florida, USA; November 5-9, 1995, pages S128, XP008019780, ISSN: 0724-8741
ALAUDDIN M M ET AL: "Evaluation of 9-[(3-F-fluoro-1-hydroxy-2-propoxy)methyl]guanine ([F]-FHPG) in vitro and in vivo as a probe for PET imaging of gene incorporation and expression in tumors - Initial evaluation with PET with the radiolabeled glucose analogue 2-(F-18)fluoro-2-deoxy-d-glucose", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US, vol. 26, no. 4, May 1999 (1999-05-01), pages 371 - 376, XP004167069, ISSN: 0969-8051
VARAGNOLO L ET AL: "F-labeled radiopharmaceuticals for PET in oncology, excluding FDG", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US, vol. 27, no. 2, February 2000 (2000-02-01), pages 103 - 112, XP004196577, ISSN: 0969-8051
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