Dsm Fine Chemicals Austria Nfg Gmbh & Co. Kg

Chemie Linz Gesellschaft M.b.h.

Dsm Chemie Linz Gmbh

Chemie Linz Gmbh

Herbert Mayrhofer

Irma Wirth

Rudolf Neuhofer

Wolfgang Skranc

Peter Poechlauer

Peter P&ouml;chlauer

Helmut Schwab

Anton Glieder

Peter Pochlauer

Peter Pöchlauer

Christoph Kratky

Ingrid Dreveny

Rodolfo Bona

Herfried Griengl

Gerald Banko

Robert Estermann

Maria Buchner

Peter Seufer-Wasserthal

Martin Fechter

Peter Riebel

New genes containing a DNA sequence coding for hydroxynitrile lyase, which genes can be prepared via a primer combination based on the DNA sequence of the 5'-region of the mdl genes from theand fromand/or a primer 2 based on the 3&#x2032;-region of the DNA sequences of one of the hydroxynitrile lyase isoenzymes fromor from, subsequent amplification with a DNA polymerase using a DNA from organisms, containing genes coding for hydroxynitrile lyase, as templates and cloning, and also recombinant proteins which can be prepared in suitable host cells by heterologous expression of the DNA sequence of said HNL genes, and proteins and fusion proteins derived therefrom and use of said proteins for preparing (R)- or (S)-cyanohydrins.

Isolated protein having hydroxynitrile lyase activity

A process for preparing enantiomer-enriched heterocyclic (R)- and (S)-cyanohydrins of the formula (I),  where R1, R2, R3, R4 independently of one another are H, an unsubstituted or substituted C&#x2013;C-alkyl, alkenyl or alkynyl radical, where one or more carbon atoms in the chain can be replaced by an oxygen atom, a nitrogen atom, a sulfur atom, an SO or an SOgroup, an unsubstituted or substituted aryl or heteroaryl radical or heterocyclic radical or halogen, hydroxyl, NR5R6, acetyl, oxo, C&#x2013;C-carbalkoxy, C&#x2013;C-carbalkoxyamino, COOR7, cyano, amide, benzoylamino or NO, R5 and R6 are H, C&#x2013;C-alkyl radical, phenyl radical, benzyl radical or COOR7, or together form a C&#x2013;C-alkylene or heteroalkylene radical, R7 is H or C&#x2013;C-alkyl, n is 0, 1, 2 or 3, X, Y and Z can be an unsubstituted or substituted carbon atom or a radical selected from the group consisting of N, O, S or NR5R6, where R5 and R6 are as defined above, SO or SO, and at least one of the radicals X, Y and Z is not a carbon atom, where the compounds of the formula (I) can have one or more double bonds in the ring, with the proviso that in a 5-membered ring the double bond is not conjugated with the &#x2014;C(OH)CN-group, and/or can be anellated and/or bridged, by reacting a ketone of the formula (II),  where R1, R2, R3, R4, X, Y, Z and n have the meanings above, with an (R)- or (S)-hydroxynitrile lyase in an organic, aqueous or two-phase system, or in emulsion, in the presence of a cyanide group donor.

Process for preparing heterocyclic (R)- and (S)-cyanohydrins

A process for preparing protected, enantiomer-enriched cyanohydrins of the formulawhere R1 and R2 independently of one another can be an unsubstituted, monosubstituted or polysubstituted C-C-alkyl, C-C-aryl, C-C-heteroaryl, C-C-alkaryl, C-C-alkylheteroaryl or C-C-aralkyl radical or an unsubstituted, monosubstituted or polysubstituted C-C-heterocycle, or C-C-alkylheterocycle or together can be an unsubstituted or substituted C-C-alkylene radical, which can contain one or more heteroatoms in the chain, or one of the radicals is hydrogen, and R3 can be an unsubstituted or substituted C-C-alkyl, C-C-aryl or C-C-heteroaryl radical, by reacting an aldehyde or ketone of the formulawhere R1 and R2 are defined as above, in the presence of an (R)- or (S)-hydroxynitrile lyase in an organic, aqueous or 2-phase system or in emulsion at a temperature of &#x2212;5 to +40&#xb0; C. with a carbonic ester nitrile of the formulawhere R3 is defined as above.

Process for preparing protected, enantiomer-enriched cyanohydrins by in-situ derivatization

New genes containing a DNA sequence coding for hydroxynitrile lyase, which genes can be prepared via a primer combination based on the DNA sequence of the 5'-region of the mdl genes fromand fromand/or a primer 2 based on the 3&#x2032;-region of the DNA sequences of one of the hydroxynitrile lyase isoenzymes fromor from, subsequent amplification with a DNA polymerase using a DNA from organisms, containing genes coding for hydroxynitrile lyase, as templates and cloning, and also recombinant proteins which can be prepared in suitable host cells by heterologous expression of the DNA sequence of said HNL genes, and proteins and fusion proteins derived therefrom and use of said proteins for preparing (R)- or (S)-cyanohydrins.

Genes containing a DNA sequence coding for hydroxynitrile lyase, recombinant proteins derived therefrom and having hydroxynitrile lyase activity, and use thereof

Process for the preparation of chiral &agr;-hydroxycarboxylic acids

Process for the preparation of optically highly pure (R)- and (S)-&agr;-hydroxycarboxylic acids, in which either isolated, impure (R)- and (S)-&agr;-hydroxycarboxylic acids prepared by acidic hydrolysis of the (R)- and (S)- cyanohydrins obtained by enzyme-catalyzed addition of a cyanide group donor to the corresponding aldehydes or ketones are recrystallized in an aromatic hydrocarbon, optionally in the presence of a cosolvent, and optically highly pure (R)- and (S)-&agr;-hydroxycarboxylic acids having an optical purity of over 98%ee are obtained or the hydrolysis solution obtained by acidic hydrolysis of the (R)- and (S)-cyanohydrins is treated directly with an aromatic hydrocarbon, optionally in combination with a cosolvent, and is then extracted at hydrolysis temperature, whereupon after cooling of the organic phase the corresponding chemically and optically highly pure (R)- and (S)-&agr;-hydroxycarboxylic acids having an optical purity of over 98%ee crystallize out.

Process for the preparation of optically and chemically highly pure (R)- or (S)-&agr;-hydroxycarboxylic acids

The invention relates to the production of (R)-enantiomeric, optically active cyanohydrins by reacting an aldehyde or a ketone with a cyanide group donor in the presence of (R) oxynitrilase, wherein a reaction mixture comprising a) an aldehyde or a ketone dissolved in an organic solvent; said organic solvent is immiscible or only slightly miscible with water, b) any aqueous R)-oxynitrilase solution and c) a cyanide group donor is stirred in such away that an emulsion is formed which remains intact until the end of the enzymatic reaction. After the enzymatic reaction has terminated, the (R)-cyanohydrin is isolated from the reaction mixture.

Method for the production of optically active cyanohydrins using r-oxynitrilase

A process for the preparation of enantiomer-enriched aminofuranones and hydroxyfuranones in which an enantiomer-enriched cyanohydrin is acylated by an acylating agent, then cyclized at 40 to 90&deg; C. in the presence of zinc or a zinc compound to the corresponding enantiomer-enriched aminofuranone, which is converted where appropriate by acid hydrolysis into the corresponding enantiomer-enriched hydroxyfuranone.

Process for preparing enantiomer-enriched amino- and hydroxyfuranones

Process for enhancement of enantioselectivity in the enzymatic separation of (R)- and (S)-enantiomers of an asymmetric alkynol, a lipase and in the presence of at least one vinyl ester, in which the acid component has at least 4 C atoms, an organic solvent and with the addition of water. Also disclosed is a process for enhancement of enantioselectivity in the enzymatic separation of (R)- and (S)-enantiomers of an alcohol with the aid of the abovementioned vinyl ester under addition of a second vinyl ester having at least 2 C atoms less in the alkyl chain than the vinyl ester used as esterifying agent.

Increased enantioselectivity of lipase catalyzed transesterification of

Resolution of asymmetric alcohols by reacting them with a vinyl, propenyl or isopropenyl ester of an alkone- or alkene-di- or tricarboxylic acid in the presence of a lipase, and the use thereof.

Enzymatic resolution of asymmetric alcohols by means of vinyl esters of

A process for the enzymatic hydrolysis of a carboxylic acid derivative by dissolving the carboxylic acid derivative in an organic solvent which is miscible with water only to a slight extent, saturation of the organic solution with water, bringing the water-saturated organic solution into contact with a hydrolase, the hydrolysis taking place, after which the reaction solution is saturated with water again and brought into contact with the hydrolase and subsequently with water again until the desired degree of conversion is achieved.

Growing community of inventors

Engerwitzdorf, Austria

Herbert Mayrhofer