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1. (WO2007074070) ENZYMATIC REDUCTION FOR PRODUCING OPTICALLY ACTIVE ALCOHOLS
Latest bibliographic data on file with the International Bureau   

Pub. No.: WO/2007/074070 International Application No.: PCT/EP2006/069680
Publication Date: 05.07.2007 International Filing Date: 13.12.2006
IPC:
C12P 17/16 (2006.01) ,C07D 333/20 (2006.01) ,C07D 333/16 (2006.01)
C CHEMISTRY; METALLURGY
12
BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
P
FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
17
Preparation of heterocyclic carbon compounds with only O, N, S, Se, or Te as ring hetero atoms
16
containing two or more hetero rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
333
Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
02
not condensed with other rings
04
not substituted on the ring sulfur atom
06
with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
14
Radicals substituted by singly bound hetero atoms other than halogen
20
by nitrogen atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
333
Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
02
not condensed with other rings
04
not substituted on the ring sulfur atom
06
with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
14
Radicals substituted by singly bound hetero atoms other than halogen
16
by oxygen atoms
Applicants: STÜRMER, Rainer[DE/DE]; DE (UsOnly)
KESSELER, Maria[DE/DE]; DE (UsOnly)
HAUER, Bernhard[DE/DE]; DE (UsOnly)
FRIEDRICH, Thomas[DE/DE]; DE (UsOnly)
BREUER, Michael[DE/DE]; DE (UsOnly)
SCHRÖDER, Hartwig[DE/DE]; DE (UsOnly)
BASF SE[DE/DE]; 67056 Ludwigshafen, DE (AllExceptUS)
Inventors: STÜRMER, Rainer; DE
KESSELER, Maria; DE
HAUER, Bernhard; DE
FRIEDRICH, Thomas; DE
BREUER, Michael; DE
SCHRÖDER, Hartwig; DE
Common
Representative:
BASF SE; 67056 Ludwigshafen, DE
Priority Data:
10 2005 062 662.923.12.2005DE
Title (EN) ENZYMATIC REDUCTION FOR PRODUCING OPTICALLY ACTIVE ALCOHOLS
(FR) REDUCTION ENZYMATIQUE POUR PRODUIRE DES ALCOOLS OPTIQUEMENT ACTIFS
(DE) ENZYMATISCHE REDUKTION ZUR HERSTELLUNG OPTISCH AKTIVER ALKOHOLE
Abstract:
(EN) The invention relates to a method for producing optically active alkanols of formula (I), in which n represents a whole number from 0 to 5; Cyc represents an optionally substituted, mononuclear or polynuclear, saturated or unsaturated, carbocyclic or heterocyclic ring; and R1 represents halogen, SH, OH, NO2, NR2R3 or NR2R3R4+X-, where R2, R3 and R4 independently of one another represent H or a low-alkyl or low-alkoxy group and X- represents a counterion. According to said method, an enzyme with a polypeptide sequence (i) SEQ ID NO: 1 or (ii), in which up to 25 % of the amino acid groups in relation to SEQ ID NO: 1 have been modified by deletion, insertion, substitution or a combination thereof and which still retains at least 50 % of the enzymatic activity of SEQ ID NO: 1, is incubated in a medium containing alkanone of formula (II), in which n, Cyc and R1 are defined as above. The compound of formula (II) is enzymatically reduced to form the compound of formula (I) and the product thus formed is isolated.
(FR) L'invention concerne un procédé pour produire des alcanols optiquement actifs de formule I dans laquelle n représente un nombre entier de 0 à 5, Cyc désigne un cycle éventuellement substitué, carbocyclique ou hétérocyclique, saturé ou non, à un ou plusieurs noyaux, R1 signifie halogène, SH, OH, NO2, NR2R3 ou NR2R3R4+X-, sachant que R2, R3 et R4 signifient indépendamment l'un de l'autre H ou un reste alkyle inférieur ou alcoxy inférieur et X- étant un ion antagoniste. Selon l'invention, on fait incuber dans un milieu contenant une alcanone de formule II, où n, Cyc et R1 ont les significations susmentionnées, une enzyme présentant une séquence polypeptidique (i) SEQ ID NO: 1 ou (ii), dans laquelle jusqu'à 25 % des restes aminoacides sont modifiés par rapport à SEQ ID N0: 1 par délétion, insertion, substitution ou par une combinaison de ces réactions, ladite séquence polypeptidique présentant encore au moins 50 % de l'activité enzymatique de SEQ ID N0: 1. Le composé de formule II est enzymatiquement réduit en composé de formule I et le produit ainsi obtenu est isolé.
(DE) Verfahren zur Herstellung von optisch aktiven-Alkanolen der Formel I worin n für einen ganzzahligen Wert von O bis 5 steht; Cyc für einen gegebenenfalls substituierten, ein-oder mehrkernigen, gesättigten oder ungesättigten, carbocyclischen oder heterocyclischen Ring steht, und R1 für Halogen, SH, OH, NO2, NR2R3 oder NR2R3R4+X- steht, wobei R2, R3 und R4 unabhängig voneinander für H oder einen Niedrigalkyl- oder Niedrigal- koxy-Rest stehen und X- für ein Gegenion steht, wobei man in einem Alkanon der Formel II worin n, Cyc und R1 die oben angegebenen Bedeutungen besitzen, enthaltenden Medium, ein Enzym mit einer Polypeptidsequenz (i) SEQ ID NO: 1 oder (ii) bei der bis zu 25% der Aminosäurereste gegenüber SEQ ID N0: 1 durch Deletion, Insertion, Substitution oder einer Kombination davon verändert sind und die noch mindestens 50% der enzymatischen Aktivität von SEQ ID N0: 1 besitzt, inkubiert, wobei die Verbindung der Formel II zur Verbindung der Formel I enzymatisch re duziert wird, und man das gebildete Produkt isoliert.
front page image
Designated States: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Office (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (EPO) (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG)
Publication Language: German (DE)
Filing Language: German (DE)