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Ep 0503832 B1 Europaisches Patentamt (19) European Patent Office Office europeenpeen des brevets EP 0 503 832 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) lntCI.6: C12P 1/00, C12P 19/24 of the grant of the patent: //(C12P1/00, C12R1:26) 12.06.1996 Bulletin 1996/24 (21) Application number: 92301853.5 (22) Date of filing: 04.03.1992 (54) Process for the preparation of 13C-labelled compounds Verfahren zur Herstellung von 13C-markierten Verbindungen Procede de preparation de composes 1 3C marques (84) Designated Contracting States: (74) Representative: Harrison, David Christopher et al DE FR GB MEWBURN ELLIS York House (30) Priority: 08.03.1991 JP 67779/91 23 Kingsway 27.02.1992 JP 75612/92 London WC2B 6HP (GB) (43) Date of publication of application: (56) References cited: 16.09.1992 Bulletin 1992/38 WO-A-89/00201 (73) Proprietor: TOKYO GAS CO., LTD. • PATENT ABSTRACTS OF JAPAN, unexamined Minato-ku Tokyo 105 (JP) applications, C field, vol. 14, no. 318, 09 July 1990, The Patent Office Japanese Govt.; p. 122 (72) Inventors: C 738 • Kato, Nobuo • PATENT ABSTRACTS OF JAPAN, unexamined Tottori-shi, Tottori-ken (JP) applications, C field, vol. 1 5, no. 64, February 1 5, • Sato, Yoshiyuki 1991; THE PATNENT OFFICE JAPANESE Tokyo (JP) GOVERNMENT, p. 78 C 806 • Shibata, Kunihiko Funabashi-shi, Chiba-ken (JP) DO CM CO 00 CO o Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice the Patent Office of the Notice of shall be filed in o to European opposition to European patent granted. opposition a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. a. 99(1) European Patent Convention). LU Printed by Jouve, 75001 PARIS (FR) EP 0 503 832 B1 Description The present invention relates to a process for preparing compounds labelled with 13C in a specific carbon position. 1 3C-labelled fructose 6-phosphate, for example, is known to be prepared by a chemical synthesis process, in which 5 a large number of reaction steps are required in order to obtain 13C-labelled fructose 6-phosphate labelled with a specifically positioned 13C, because fructose has four asymmetric carbon atoms, giving 16 different optical isomers, resulting in a product having not very high optical purity. JP-A 130692/87 discloses a process for producing isotope labelled biochemicals which comprises cultivating a methylotrophic microorganism in a nutrient medium containing a growth carbon source comprising a 13C-|-compound. 10 JP-A 130692/87 discloses a bioconversion process which comprises cultivating a methylotrophic microorganism (or cell extract thereof) in a nutrient medium containing an assimilable Cn-compound and a 13C1 -compound to produce an accumulated quantity of 13C-labelled Cn+1 -condensation product, wherein n is an integer with a value of at least 2. JP-A-1 30692/87 discloses on page 5, right upper column, lines 8-1 2, that the term "ribulose monophosphate path- way" (RMP) as employed herein refers to the biochemical cycle in which three molecules of formaldehyde are con- 's densed to produce either one molecule of pyruvate or one molecule of dihydroxyacetone phosphate, and further teach- es on page 7, left lower column, line 16 to right lower column, line 5, that hexulose 6-phosphate is the product of hexulose phosphate synthase activity and that hexulose phosphate isomerase converts hexulose 6-phosphate to glu- cose 6-phosphate. However, that disclosure neither teaches nor suggest a process for preparing 13C-labelled fructose 6-phosphate 20 or 13C-labelled glucose 6-phosphate specifically labelled with 13C in a carbon position C-l from ribose 5-phosphate and 13C-labelled methanol or 13C-labelled formaldehyde in the presence of a specific series of enzymes. JP-A-1 30692/87 exemplifies preparation of an exopolysaccharide containing 13C-glucose as a main constituent by carrying out fermentation using 13C-methanol as a growth carbon source, resulting in producing 13C-glucose uni- formly labelled with 13C it being impossible to obtain 13C-labelled glucose, specifically labelled with 13C in a carbon 25 position C-1. WO-A-89/00201 discloses the production of isotopically-labelled (eg. 13C) organic compounds in cell culture using a mutart cell strain capable of producing the organic compound of interest and at least one simple labelled inorganic nutrient as the isotope source. The use of 13C-labelled compounds with 13C in a specific carbon position makes it possible in the case for studies 30 on a biological energy metabolism pathway by use of nuclear magnetic resonance apparatus, mass spectrometer, etc. to provide more usefuf qualitative and quantitative information than in the case of use of compounds uniformly labelled with 13C, 14C-labelled compounds, and the like; thus, compounds labelled with 13C in a specific carbon position are applicable to various fields ranging from studies on biological reactions to medical services. Development of an indus- trially advantageous process for the preparation thereof is highly desirable. 35 For example, fructose 6-phosphate or glucose 6-phosphate is a metabolic intermediate in the glycolitic pathway and is useful for studies of the biological energy metabolism pathway, and 13C-labelled fructose 6-phosphate or Re- labelled glucose 6-phosphate specifically labelled with 13C in a specific carbon position is preferable to uniformly la- belled ones for tracing the conversion of fructose 6-phosphate or glucose 6-phosphate in vivo by use of a mass spec- trometer, nuclear magnetic resonance apparatus, etc. 40 It is an object of the present invention to provide an industrially advantageous process for the preparation of Re- labelled compounds labelled with 13C in a specific carbon position, for example, 13C-labelled fructose 6-phosphate or 13C-labelled glucose 6-phosphate specifically labelled with 13C in carbon position C-1. A first aspect of the present invention provides a process for preparing a 13C-labelled compound which comprises reacting an alcohol 13C-labelled carbon source compound and a substrate in the presence of an enzyme system con- 45 sisting of oxidase belonging to EC1 group and capable of converting the alcohol 13C-labelled carbon source compound to an aldehyde 13C-labelled carbon source compound, lyase belonging to EC4 group and capable of synthesizing a carbon-carbon bond and at least one of isomerases belonging to EC5 group and capable of isomerizing substrates to obtain a 13C-labelled compound specifically labelled with 13C in a specific carbon position. A second aspect of the present invention provides a process for preparing a 13C-labelled compound which corn- so prises isomerizing a substrate in the presence of a first isomerase to form an isomerized substrate, reacting the isomer- ized substrate in the presence of lyase with an aldehyde 13C-labelled carbon source compound formed by oxidizing an alcohol 13C-labelled carbon source compound in the presence of oxidase to obtain a condensate labelled with 13C in a specific carbon position, and isomerizing the condensate in the presence of a second isomerase to obtain a first isomer labelled with 13C in a specific carbon position and preferably further comprises isomerizing the first isomer in 55 the presence of a third isomerase to obtain a second isomer, preferably said oxidase being used in combination with catalase and hydrogen peroxide. A preferred embodiment of the first aspect of the present invention provides a process comprises reacting ribose 5-phosphate with 13C-labelled methanol in the presence of alcohol oxidase and of a formaldehyde-fixing enzyme sys- 2 EP 0 503 832 B1 tem obtained from microorganisms growing on methanol and consisting of phosphoriboisomerase, hexulose phosphate synthase and phosphohexuloisomerase to obtain 13C-labelled fructose 6-phosphate specifically labelled with 13C in carbon position C-1 . A preferred embodiment of the second aspect of the present invention provides a process comprises isomerizing 5 ribose 5-phosphate in the presence of phosphoriboisomerase to form ribulose 5-phosphate, reacting the ribulose 5-phosphate in the presence of hexulose phosphate synthase with 13C-labelled formaldehyde formed by oxidizing Re- labelled methanol in the presence of alcohol oxidase to form 13C-labelled hexulose 6-phosphate, and isomerizing Re- labelled hexulose 6-phosphate in the presence of phosphohexuloisomerase to form RC-labelled fructose 6-phosphate specifically labelled with 13C in carbon position C-1 . 10 Another preferred embodiment of the present invention provides a process comprises reacting ribose 5-phosphate with RC-labelled methanol in the presence of alcohol oxidase and of a formaldehyde-fixing enzyme system obtained from microorganisms growing on methanol and consisting of phosphoriboisomerase, hexulose phosphate synthase, phosphohexuloisomerase and phosphoglucoisomerase to obtain RC-labelled glucose 6-phosphate specifically la- belled with RC in carbon position C-1 . is Another preferred embodiment of the second aspect of the present invention provides a process comprises isomer- izing ribose 5-phosphate in the presence of phosphoriboisomerase to form ribulose 5-phosphate, reacting the ribulose 5-phosphate in the presence of hexulose phosphate synthase with RC-labelled formaldehyde formed by oxidizing Re- labelled methanol in the presence of alcohol oxidase to form RC-labelled hexulose 6-phosphate, isomerizing Re- labelled hexulose 6-phosphate in the presence of phosphohexuloisomerase
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