Enzyme process for the preparation of lipoamino acids of the alkyl amide and ester type

• Main Authors: CLAPES SABORIT PERE, MORAN BADENAS CARMEN, INFANTE MARTINEZ PARDO M. ROSA
• Format: Patent
• Language: English; Spanish
• Published: 01.07.1999
• Edition: 6
• Subjects: ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; BEER; BIOCHEMISTRY; CANDLES; CHEMISTRY; DETERGENT COMPOSITIONS; DETERGENTS; ENZYMOLOGY; FATTY ACIDS THEREFROM; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE; METALLURGY; MICROBIOLOGY; MUTATION OR GENETIC ENGINEERING; RECOVERY OF GLYCEROL; RESIN SOAPS; SOAP OR SOAP-MAKING; SPIRITS; USE OF SINGLE SUBSTANCES AS DETERGENTS; VINEGAR; WINE

Enzyme process for the preparation of lipoamino acids of the alkyl amide and ester type. This relates to a process for the synthesis of single- chain lipid derivatives of amino acids of general formula H2N-CHR1-CO-NH-R2 and H2N-CHR1-CO-O-R2, where R1 may be a hydrogen, a straight or branched optionally substituted saturated or unsaturated chain or an optionally substituted aromatic group and R2 is an alkyl chain of any length. It involves the use of hydrolytic enzyme to form amide and ester links between an amino acid derivative and an alkyl amine or alcohol respectively. The advantages offered are fundamentally that it eliminates the production of undesirable by-products, that it is stereospecific (regionally selective and enantioselective), the operating conditions are mild and it can be scaled to industrial level. For this reason this new process can be an alternative to the conventional synthesis for the preparation of these surfactants of natural origin and low toxicity. Procedimiento enzimático para la preparación de lipoaminoácidos del tipo alquil amidas y ésteres. Se trata de un procedimiento para la síntesis de derivados lipídicos monocatenarios de aminoácidos de fórmula general H sub,2 N-CHR sub,1 -CO-NH-R sub,2 y H sub,2 N-CHR sub,1 -CO-O-R sub,2 , donde R sub,1 puede ser un hidrógeno, una cadena lineal o ramificada opcionalmente substituida, saturada o no saturada, o un grupo aromático opcionalmente substituido; y R sub,2 una cadena alquílica de cualquier longitud. Se trata de la utilización de enzima hidrolíticos para la formación de los enlaces amida y éster entre un derivado de aminoácido y una alquil amina o alcohol respectivamente. Las ventajas que ofrece, son fundamentalmente: elimina la formación de subproductos indeseables, en estereoespecífica (regio y enantioselectiva), condiciones suaves de operación y escalable a nivel industrial. Es por ello que este nuevo procedimiento puede ser una alternativa a la síntesis convencional de cara a la preparación de estos tensioactivos de origen natural y baja toxicidad.