Synthesis of indigo and 2,2'-bis(3-oxo-pyrrolo(2,3-b)pyridylidene) compounds, used for coloring keratinous fibers, e.g. human hair, involves enzymatic conversion and oxidation of tryptophan derivative with tryptophanase then oxidase

摘要

Synthesis of indigo and 2,2'-bis(3-oxo-pyrrolo(2,3-b)pyridylidene) compounds (I) comprises (1) enzymatic conversion of a tryptophan derivative (II) with a tryptophanase enzyme in the presence of pyridoxal phosphate at 10-50 deg C and then (2) enzymatic oxidation to (I) in the presence of NADH (hydrated form of beta -nicotinamide-adenine dinucleotide acting as cofactor) and a suitable oxidase enzyme at 10-50 deg C. Synthesis of indigo and 2,2'-bis(3-oxo-pyrrolo(2,3-b)pyridylidene) compounds of formula (I) comprises: (1) enzymatic conversion of a tryptophan derivative of formula (II) with a tryptophanase enzyme in the presence of pyridoxal phosphate at 10-50 deg C; and then (2) enzymatic oxidation to (I) in the presence of NADH (hydrated form of beta -nicotinamide-adenine dinucleotide acting as cofactor) and a suitable oxidase enzyme at 10-50 deg C; X = nitrogen (N) or a methin group, CR4; R = hydrogen (H) or 1-4 carbon (C) alkyl; R1-4 = H, linear or branched 1-6 C alkyl, aryl, difluoromethyl, trifluoromethyl, halogen (fluorine (F), chlorine (Cl), bromine (Br) or iodine (I), amino, 1-6 C alkylamino, arylamino, hydroxyl, 1-4 C alkoxy, aryloxy, nitro, carboxy, carboxyalkyl, carboxamido, carboalkoxy, carboaryloxy or heterocyclyl; or R1R2 or R2R3 = methylenedioxy; R1-3 not = H in at least one case if X = CH. Independent claims are also included for multicomponent colorants for keratinous fibers.