ES2534657T3 - Oxidorreductasas para la reducción estereoselectiva de compuestos cetónicos - Google Patents

Oxidorreductasas para la reducción estereoselectiva de compuestos cetónicos Download PDF

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ES2534657T3
ES2534657T3 ES11189708.8T ES11189708T ES2534657T3 ES 2534657 T3 ES2534657 T3 ES 2534657T3 ES 11189708 T ES11189708 T ES 11189708T ES 2534657 T3 ES2534657 T3 ES 2534657T3
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oxidoreductases
nucleic acid
acid sequence
oxidoreductase
ketone compounds
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Anke Tschentscher
Antje Gupta
Maria Dupont
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Cambrex IEP GmbH
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Cambrex IEP GmbH
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
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    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/52—Genes encoding for enzymes or proenzymes
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    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C12N9/0008—Oxidoreductases (1.) acting on the aldehyde or oxo group of donors (1.2)
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • C—CHEMISTRY; METALLURGY
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    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/42—Hydroxy-carboxylic acids

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  • Chemical & Material Sciences (AREA)
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Abstract

Procedimiento para la reducción enzimática enantioselectiva de un compuesto cetónico para dar el correspondiente compuesto de hidroxilo quiral, en el que el compuesto cetónico se reduce en presencia de un cofactor con una oxidorreductasa, caracterizado porque se usa una oxidorreductasa que se selecciona del grupo que está constituido por las oxidorreductasas para las que (a) codifica la secuencia de ácido nucleico SEC ID N.º: 14, o (b) codifica una secuencia de ácido nucleico cuya cadena complementaria se hibrida con la secuencia de ácido nucleico mencionada en (a) en condiciones altamente rigurosas.

Description

imagen1
imagen2
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E11189708
09-04-2015
de reacción de medición patrón de acuerdo con el ejemplo 1 con distintos sustratos. La actividad con acetoacetato de metilo se fijó para todas las enzimas igual al 100 % y todos los otros sustratos se fijaron en proporción con respecto a ésta. Tabla 9: Reducción de los espectros de sustrato
Sustrato
Gordonia rubripertincta SEC ID N.º 6
1-Fenil-2-propanona
82%
Cloruro de fenacilo
7 %
Acetofenona
23 %
Acetonaftona
68 %
Butirofenona
0%
2-Octanona
75 %
3-Octanona
52 %
2-Butanona
14 %
2-Oxovaleriato de etilo
23 %
Ácido etil-2-oxo-4-fenilbutírico
18 %
Piruvato de etilo
160 %
Fenilglioxilato de etilo
11 %
4-Cloroacetoacetato de etilo
110 %
Acetoacetato de metilo
100 %
3-Oxovaleriato de etilo
56 %
Acetona
7 %
5
7f: Estabilidad en el sistema de dos fases acuoso/orgánico
La estabilidad de las oxidorreductasas novedosas en sistemas de dos fases acuoso/orgánicos se sometió a estudio diluyendo los lisados obtenidos en el ejemplo 6 (de expresión recombinante) en un tampón acuoso adecuado para la respectiva oxidorreductasa (aproximadamente 10 unidades/ml de tampón). A la oxidorreductasa diluida en el tampón 10 se añadió entonces el mismo volumen de un disolvente orgánico, no miscible con agua y la mezcla de reacción se incubó a temperatura ambiente con mezclado constante (termomezclador con 170 rpm). Tras incubación durante 24 h se extrajeron respectivamente de la fase acuosa 10 l y se usaron para la determinación de la actividad enzimática en la mezcla de reacción de prueba patrón (tampón fosfato de potasio (KPP) 100 mM, pH = 7,0, NAD(P)H 0,2 mM, sustrato 10 mM). También en este caso se fijó el valor de partida directamente tras dilución en el tampón igual al 100
15 % y todos los otros valores se fijaron en proporción con respecto a éste.
Tabla 9: Actividad enzimática tras incubación durante 24 h en el sistema de dos fases acuoso-orgánico
Sistema
Tampón Acetato de butilo Dietiléter MTBE Diisopropiléter Heptano Ciclohexano
Gordonia rubripertincta SEC ID N.º 6
100 % 80-100 % 80-100 % 80100 % 80-100 % 80-100 % 80-100 %
MTBE = metil-terc-butiléter
12

Claims (1)

  1. imagen1
ES11189708.8T 2005-07-27 2006-07-20 Oxidorreductasas para la reducción estereoselectiva de compuestos cetónicos Active ES2534657T3 (es)

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AT12612005 2005-07-27
AT0126105A AT502395B1 (de) 2005-07-27 2005-07-27 Oxidoreduktasen zur stereoselektiven reduktion von ketoverbindungen

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JP (1) JP2009502148A (es)
KR (2) KR101354546B1 (es)
CN (1) CN101273137A (es)
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CA2821719A1 (en) 2007-02-01
KR20080036617A (ko) 2008-04-28
US20140017743A1 (en) 2014-01-16
CA2821720C (en) 2015-11-24
EP2428576A1 (de) 2012-03-14
DK2426209T3 (da) 2014-11-10
KR20130110223A (ko) 2013-10-08
ES2525549T3 (es) 2014-12-26
PT2428576E (pt) 2015-04-30
SI2428576T1 (sl) 2015-04-30
EP2428575A1 (de) 2012-03-14
EP2428574B1 (de) 2014-09-24
SI2428574T1 (sl) 2014-12-31
JP2009502148A (ja) 2009-01-29
CN101273137A (zh) 2008-09-24
AT502395B1 (de) 2007-03-15
US20090311762A1 (en) 2009-12-17
AU2006274252A1 (en) 2007-02-01
PL2426209T3 (pl) 2015-04-30
SI2426209T1 (sl) 2015-02-27
CA2625834C (en) 2013-08-27
EP2426209A1 (de) 2012-03-07
WO2007012428A1 (de) 2007-02-01
CA2821717A1 (en) 2007-02-01
EP2428574A1 (de) 2012-03-14
EP2428576B1 (de) 2015-01-14
CA2821720A1 (en) 2007-02-01
EP1907556A1 (de) 2008-04-09
KR101354546B1 (ko) 2014-01-22
CA2869218C (en) 2017-06-27
HUE024985T2 (hu) 2016-02-29
DK2428574T3 (da) 2014-10-27
CA2821719C (en) 2017-06-27
CA2625834A1 (en) 2007-02-01
EP2426209B1 (de) 2014-10-15
DK2428576T3 (en) 2015-03-09
ZA200800732B (en) 2009-05-27
CA2869218A1 (en) 2007-02-01
US9040265B2 (en) 2015-05-26
ES2524167T3 (es) 2014-12-04
AU2006274252B2 (en) 2012-12-13
AT502395A4 (de) 2007-03-15
PL2428576T3 (pl) 2015-07-31
KR101341392B1 (ko) 2013-12-20
PL2428574T3 (pl) 2015-03-31
PT2428574E (pt) 2014-11-26
CA2821717C (en) 2017-06-27
PT2426209E (pt) 2014-12-16

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