WO2005116232A1 - Method for the synthesis of nucleosides using psychrotolerant or psychrotrophic micro-organisms - Google Patents

Method for the synthesis of nucleosides using psychrotolerant or psychrotrophic micro-organisms Download PDF

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Publication number
WO2005116232A1
WO2005116232A1 PCT/ES2005/000166 ES2005000166W WO2005116232A1 WO 2005116232 A1 WO2005116232 A1 WO 2005116232A1 ES 2005000166 W ES2005000166 W ES 2005000166W WO 2005116232 A1 WO2005116232 A1 WO 2005116232A1
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procedure
microorganisms
whole cells
microorganism used
synthesized
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PCT/ES2005/000166
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Spanish (es)
French (fr)
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Jose Vicente Sinisterra Gago
Luis Alberto Condezo Hoyos
Jesús FERNÁNDEZ_LUCAS
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Universidad Complutense De Madrid
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Publication of WO2005116232A1 publication Critical patent/WO2005116232A1/en

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    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/26—Preparation of nitrogen-containing carbohydrates
    • C12P19/28—N-glycosides
    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/26—Preparation of nitrogen-containing carbohydrates
    • C12P19/28—N-glycosides
    • C12P19/38—Nucleosides
    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/26—Preparation of nitrogen-containing carbohydrates
    • C12P19/28—N-glycosides
    • C12P19/38—Nucleosides
    • C12P19/40—Nucleosides having a condensed ring system containing a six-membered ring having two nitrogen atoms in the same ring, e.g. purine nucleosides

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention relates to a method for the synthesis of nucleosides from uracil nucleosides, using 2'-deoxyribosyltransferase or phosphorylase nucleoside producing psychrotrophic micro-organisms. According to the invention, the reaction temperature is less than 60 °C and preferably 57 °C. The micro-organisms used comprise psychrotrophic strains of Bacillus subtilis ssp. Niger, Bacillus psychrosaccharolyticus, Photobacterium phosphoreum and Psychrobacter immobilis. When the aforementioned synthesis is performed at lower-than-normal temperatures, different nucleosides are obtained with little secondary product formation.

Claims

Reivindicaciones Claims
1. Procedimiento para la síntesis en un único paso de nucleósidos purínicos, pirimidínicos, o con otros heterociclos relacionados, por intercambio de bases caracterizado porque emplea células de microorganismos psicrotrofos a una temperatura de reacción entre 45 y 75 °C.1. Procedure for the synthesis in a single step of purine nucleosides, pyrimidines, or with other related heterocycles, by base exchange characterized in that it uses cells of psychrotrophic microorganisms at a reaction temperature between 45 and 75 ° C.
2. Procedimiento, según reivindicación 1, caracterizado porque la temperatura de reacción es de 57 °C.2. Process according to claim 1, characterized in that the reaction temperature is 57 ° C.
3. Procedimiento, según reivindicaciones anteriores, caracterizado porque el microorganismo utilizado es Aeromonas salmonicida ssp achromogenes.3. Procedure, according to previous claims, characterized in that the microorganism used is Aeromonas salmonicida ssp achromogenes.
4. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el microorganismo utilizado es Bacillus psychrosaccharolyticus.4. Procedure, according to claims 1 and 2, characterized in that the microorganism used is Bacillus psychrosaccharolyticus.
5. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el microorganismo utilizado es Bacillus subtilis ssp. niger.5. Procedure according to claims 1 and 2, characterized in that the microorganism used is Bacillus subtilis ssp. Niger.
6. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el microorganismo utilizado es Photobacterium damselae.6. Procedure, according to claims 1 and 2, characterized in that the microorganism used is Photobacterium damselae.
7. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el microorganismo utilizado es Photobacterium leiognathi.7. Procedure, according to claims 1 and 2, characterized in that the microorganism used is Photobacterium leiognathi.
8. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el microorganismo utilizado es Photobacterium phosphoreum.8. Procedure, according to claims 1 and 2, characterized in that the microorganism used is Photobacterium phosphoreum.
9. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el microorganismo utilizado es Psychrobacter immobilis. 9. Procedure, according to claims 1 and 2, characterized in that the microorganism used is Psychrobacter immobilis.
10. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el microorganismo utilizado es Vibrio alginolyticus.10. Procedure according to claims 1 and 2, characterized in that the microorganism used is Vibrio alginolyticus.
11. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el microorganismo utilizado es Vibrio mediterranei.11. Procedure, according to claims 1 and 2, characterized in that the microorganism used is Vibrio mediterranei.
12. Procedimiento, según reivindicaciones anteriores, caracterizado porque los nucleósidos sintetizados son ribonucleósidos purínicos, pirimidínicos o con otros heterociclos relacionados que se obtienen a partir de ribonucleósidos de uridina.12. Process according to previous claims, characterized in that the synthesized nucleosides are purine, pyrimidine or other related heterocycles ribonucleosides that are obtained from uridine ribonucleosides.
13.- Procedimiento, según reivindicaciones 1 y 2, caracterizado porque los nucleósidos sintetizados son 2'-deoxiribonucleósidos purínicos, pirimidínicos o con otros heterociclos relacionados obtenidos a partir de 2'-deoxiuridina o timidina.13. Method according to claims 1 and 2, characterized in that the synthesized nucleosides are purine, pyrimidine or 2'-deoxyribonucleosides or with other related heterocycles obtained from 2'-deoxyuridine or thymidine.
14. Procedimiento, según reivindicación 13, caracterizado porque emplea células enteras de los microorganismos relacionados en las reivindicaciones 4 a 9.14. Method according to claim 13, characterized in that it uses whole cells of the microorganisms related in claims 4 to 9.
15. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque los nucleósidos sintetizados son 2',3'-dideoxiribonucleósidos purínicos, pirimidínicos o con otros heterociclos relacionados obtenidos a partir de 2', 3'- dideoxiuridina.15. Method according to claims 1 and 2, characterized in that the synthesized nucleosides are purine, pyrimidine or 2 ', 3'-dideoxyribonucleosides or with other related heterocycles obtained from 2', 3'-dideoxyuridine.
16. Procedimiento, según reivindicación 15, caracterizado porque emplea células enteras de los microorganismos relacionados en las reivindicaciones 3 a 11.16. Method according to claim 15, characterized in that it uses whole cells of the microorganisms related in claims 3 to 11.
17. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el nucleósido sintetizado es el ribonucleótido del 3-carboxamido-1 ,2,4-triazol y se obtiene a partir de uridina. 17. Method according to claims 1 and 2, characterized in that the synthesized nucleoside is the ribonucleotide of 3-carboxamido-1, 2,4-triazole and is obtained from uridine.
18. Procedimiento, según reivindicación 17, caracterizado porque emplea células enteras de los microorganismos relacionados en la reivindicación 5.18. Method according to claim 17, characterized in that it uses whole cells of the microorganisms related in claim 5.
19. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el nucleósido sintetizado es el ribonucleósido de 6-mercaptopurina y se obtiene a partir de uridina.19. Method according to claims 1 and 2, characterized in that the synthesized nucleoside is the ribonucleoside of 6-mercaptopurine and is obtained from uridine.
20. Procedimiento, según reivindicación 19, caracterizado porque emplea células enteras de los microorganismos relacionados en la reivindicación 5.20. Method according to claim 19, characterized in that it uses whole cells of the microorganisms related in claim 5.
21. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el nucleósido sintetizado es el 2'-deoxiribonucleósido de 6-mercaptopurina y se obtiene a partir de 2'-deoxiuridina.21. Process according to claims 1 and 2, characterized in that the synthesized nucleoside is 2'-deoxyribonucleoside of 6-mercaptopurine and is obtained from 2'-deoxyuridine.
22. Procedimiento, según reivindicación 21, caracterizado porque emplea células enteras de los microorganismos relacionados en la reivindicación 5.22. Procedure according to claim 21, characterized in that it uses whole cells of the microorganisms related in claim 5.
23. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el nucleósido sintetizado es el 2'-deoxiribonucleósido de 6-mercaptopurina y se obtiene a partir de 2'-deoxiuridina.23. Process according to claims 1 and 2, characterized in that the synthesized nucleoside is the 2'-deoxyribonucleoside of 6-mercaptopurine and is obtained from 2'-deoxyuridine.
24. Procedimiento, según reivindicación 23, caracterizado porque emplea células enteras de los microorganismos relacionados en la reivindicación 5.24. Method according to claim 23, characterized in that it uses whole cells of the related microorganisms in claim 5.
25. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el nucleósido sintetizado es 2',3'-dideoxiadenosina y se obtiene a partir de 2',3'-dideoxiuridina.25. Process according to claims 1 and 2, characterized in that the synthesized nucleoside is 2 ', 3'-dideoxydenosine and is obtained from 2', 3'-dideoxyuridine.
26. Procedimiento, según reivindicación 25, caracterizado porque emplea células enteras de los microorganismos relacionados en la reivindicación 5. 26. The method according to claim 25, characterized in that it uses whole cells of the related microorganisms in claim 5.
27. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el nucleósido sintetizado es el 2'-deoxiribonucleósido de 5'-fluoruracilo y se obtiene a partir de 2'-deoxiuridina.27. The method according to claims 1 and 2, characterized in that the synthesized nucleoside is 2'-deoxyribonucleoside of 5'-fluoruracil and is obtained from 2'-deoxyuridine.
28. Procedimiento, según reivindicación 27, caracterizado porque emplea células enteras de los microorganismos relacionados en la reivindicación 4.28. The method according to claim 27, characterized in that it uses whole cells of the microorganisms related in claim 4.
29. Procedimiento, según reivindicaciones 1 y 2, caracterizado porque el nucleósido sintetizado es el 2'-deoxiribonucleósido de 5'-clorouracilo y se obtiene a partir de 2'-deoxiuridina.29. Process according to claims 1 and 2, characterized in that the synthesized nucleoside is 2'-deoxyribonucleoside of 5'-chlorouracil and is obtained from 2'-deoxyuridine.
30. Procedimiento, según reivindicación 29, caracterizado porque emplea células enteras de los microorganismos relacionados en la reivindicación 4. 30. The method according to claim 29, characterized in that it uses whole cells of the related microorganisms in claim 4.
PCT/ES2005/000166 2004-04-02 2005-03-30 Method for the synthesis of nucleosides using psychrotolerant or psychrotrophic micro-organisms WO2005116232A1 (en)

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ESP200400817 2004-04-02
ES200400817A ES2241487B2 (en) 2004-04-02 2004-04-02 PROCEDURE FOR SYNTHESIS OF NUCLEOSIDS BY USING PSYCHROTROPHIC OR PSYCHROTOLERANT MICROORGANISMS.

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4458016A (en) * 1981-03-09 1984-07-03 Ajinomoto Co., Inc. Production of 1-β-D-ribofuranosyl-1,2,4-triazole
US4614719A (en) * 1982-04-30 1986-09-30 Yamasa Shoyu Kabushiki Kaisha Process for producing ribavirin

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4458016A (en) * 1981-03-09 1984-07-03 Ajinomoto Co., Inc. Production of 1-β-D-ribofuranosyl-1,2,4-triazole
US4614719A (en) * 1982-04-30 1986-09-30 Yamasa Shoyu Kabushiki Kaisha Process for producing ribavirin

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CAVICCHIOLI R. ET AL: "Low-temperature extremophiles and their applications", CURRENT OPINION IN BIOTECHNOLOGY, vol. 13, no. 3, 2002, pages 253 - 261 *
LEWKOWICZ E.S. ET AL: "An improved microbial synthesis of purine nucleosides", BIOTECHNOLOGY LETTERS, vol. 22, 2000, pages 1277 - 1280 *
RAMANA K.V. ET AL: "Biotechnological application of psycrophiles and their habitat to low-temperature", JOURNAL OF SCIENTIFIC AND INDUSTRIAL RESEARCH, vol. 59, 2000, pages 87 - 101 *
RUSSEL N.J.: "Toward a molecular understanding of cold activity of enzimes from psycrophiles", EXTREMOPHILES, vol. 4, 2000, pages 83 - 90 *
TRELLES J.A. ET AL: "Purine nucleoside synthesis from uridine using immobilised Enterobacter gergoviae CECT 875 whole cells", TETRAHEDRON LETTERS, vol. 44, no. 12, 2003, pages 2605 - 2609 *

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ES2241487A1 (en) 2005-10-16

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