Process for preparing D-(-)-N-carbamoyl-2-(phenyl or substituted phenyl)glycines
AssigneeKanegafuchi Kagaku Kogyo Kabushiki Kaisha
InventorsHideaki Yamada, Satomi Takahashi, Koji Yoneda
Life of this patent
Estimating the term…
Abstract
A process for preparing D-(-)-N-carbamoyl-2-(phenyl or substituted phenyl)glycines by subjecting 5-(phenyl or substituted phenyl)hydantoins to the action of a cultured broth, cells or treated cells of microorganisms having a capability in asymmetrically hydrolyzing the hydantoin ring. D-(-)-N-carbamoyl-2-(phenyl or substituted phenyl)glycines are useful intermediates of medicines and can be readily converted to D-(-)-2-(phenyl or substituted phenyl) glycines known as available intermediates of antibiotics.
Claims13
A process for preparing D-(-)-N-carbamoyl-2-(phenyl or substituted phenyl)glycines having the following general formula:
- ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen atom, a halogen atom, hydroxyl group, a lower alkoxyl group or methyl group,
- which comprises subjecting 5-(phenyl or substituted phenyl)hydantoins having the following general formula:
- ##STR4## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above to the action of an enzyme which is in the form of a cultured broth containing microorganisms or the separated cells of said microorganisms in an aqueous medium, said enzyme being capable of hydrolyzing 5-(phenyl or substituted phenyl)hydantoins so as to substantially produce only D-(-)forms of N-carbamoyl-2-(phenyl or substituted phenyl)-glycines, and recovering said D-carbamoyl glycines from the medium.
A process for preparing D-(-)-N-carbamoyl-2-phenylglycine which comprises subjecting DL-5-phenylhydantoin to the action of an enzyme which is in the form of a cultured broth containing microorganisms, the separated cells of said microorganisms, the immobilized separated cells of said microoganisms or the immobilized separated cells of said microorganisms that have been cultured in the presence of a hydantoin compound, in an aqueous reaction medium of pH 7 to 10, said enzyme being capable of hydrolyzing 5-(phenyl or substituted phenyl)hydantoins so as to substantially produce only D-(-)forms of N-carbamoyl-2-(phenyl or substituted phenyl)-glycines, and recovering said D-carbamoyl glycines from the medium, said microorganism being one member selected from the group consisting of Aerobacter, Agrobacterium, Brevibacterium, Corynebacterium, Microbacterium, Micrococcus, Pseudomonas, Actinoplanes, Mycobacterium, Nocardia and Streptomyces.
A process for preparing D-(-)-N-carbamoyl-2-(hydroxyphenyl)glycine which comprises subjecting DL-5-(hydroxyphenyl)hydantoin to the action of an enzyme which is in the form of a cultured broth containing microorganisms, the separated cells of said microorganisms, the immobilized separated cells of said microorganisms or the immobilized separated cells of said microoganisms that have been cultured in the presence of a hydantoin compound, in an aqueous reaction medium of pH 7 to 10, said enzyme being capable of hydrolyzing 5-(phenyl or substituted phenyl)hydantoins so as to substantially produce only D-(-)forms of N-carbamoyl-2-(phenyl or substituted phenyl)-glycines, and recovering said D-carbamoyl glycines from the medium, said microorganism being one member selected from the group consising of Aerobacter, Agrobacterium, Brevibacterium, Corynebacterium, Microbacterium, Micrococcus, Pseudomonas, Actinoplanes, Mycobacterium, Nocardia and Streptomyces.
A process for preparing D-(-)-N-carbamoyl-2-(methoxyphenyl)glycine which comprises subjecting DL-5-(methoxyphenyl)hydantoin to the action of an enzyme which is in the form of a cultured broth containing microorganisms, the separated cells of said microorganisms, the immobilized separated cells of said microorganisms or the immobilized separated cells of said microorganisms that have been cultured in the presence of a hydantoin compound, in an aqueous reaction medium of pH 7 to 10, said enzyme being capable of hydrolyzing 5-(phenyl or substituted pheny)hydantoins so as to substantially produce only D-(-)forms of N-carbamoyl-2-(phenyl or substituted phenyl)-glycines, and recovering said D-carbamoyl glycines from the medium, said microorganism being one member selected from the group consisting of Aerobacter, Agrobacterium, Brevibacterium, Corynebacterium, Microbacterium, Micrococcus, Pseudomonas, Actinoplanes, Mycobacterium, Nocardia and Streptomyces.
Dependencies are inferred from the claim text.