Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing nitrogen-containing organic compound
Patent
1997-04-04
1998-03-10
Saucier, Sandra E.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing nitrogen-containing organic compound
435280, 435822, 435911, C12P 1302
Patent
active
057260478
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for producing optically active 1-halo-3-amino-4-phenyl-2-butanol derivatives and, more particularly, to an efficient process for producing optically active 1-halo-3-amino-4-phenyl-2-butanol derivatives by bringing the corresponding optically active 1-halo-3-amino-4-phenyl-2-butanone derivatives into contact with a microorganism to thereby cause stereoselective reduction of said butanone derivatives.
In particular, the present invention relates to an efficient process for producing (2S,3S)-1-halo-3-amino-4-phenyl-2-butanol derivatives by bringing the corresponding (3S)-1-halo-3-amino-4-phenyl-2-butanone derivatives into contact with a specific microorganism. Optically active 1-halo-3-amino-4-phenyl-2-butanol derivatives, in particular (2S,3S)-1-halo-3-amino-4-phenyl-2-butanol derivatives, are useful as intermediates for the production of optically active medicinal compounds such as HIV protease inhibitors, as is disclosed in Japanese Kokai Publication Hei-03-252563.
BACKGROUND ART
A process is known for the production of (2S,3S)-1-halo-3-amino-4-phenyl-2-butanol derivatives which comprises reducing chemically amino-protected (3S)-1-halo-3-amino-4-phenyl-2-butanone derivatives with a reducing agent such as sodium borohydride (Japanese Kokai Publication Hei-02-42048; Tetrahedoron, 50, 6333, 1994). However, no reports have so far dealt with a process for producing (2S,3S)-1-halo-3-amino-4-phenyl-2-butanol derivatives by causing a microorganism to act on (3S)-1-halo-3-amino-4-phenyl-2-butanone derivatives.
The above-mentioned process comprising reducing amino-protected (3S)-1-halo-3-amino-4-phenyl-2-butanone derivatives with a reducing agent such as sodium borohydride requires the use of such a relatively expensive reducing agent and, moreover, is unsatisfactory from the stereoselectivity viewpoint.
SUMMARY OF THE INVENTION
In view of the foregoing, the present invention has for its object to provide a process of reducing optically active 1-halo-3-amino-4-phenyl-2-butanone derivatives to the corresponding optically active 1-halo-3-amino-4-phenyl-2-butanol derivatives stereoselectively with good yields.
The gist of the present invention consists in that optically active 1-halo-3-amino-4-phenyl-2-butanol derivatives are produced by bringing an optically active 1-halo-3-amino-4-phenyl-2-butanone derivative of the general formula (1); ##STR1## (wherein X represents a halogen atom. R.sup.1 and R.sup.2 each independently represents a hydrogen atom, a hydroxyl group which is optionally protected, an alkoxyl group, an alkyl group, a nitro group, an amino group which is optionally protected, or a cyano group. P.sup.1 and P.sup.2 each independently represents a hydrogen atom or an amino-protecting group or P.sup.1 and P.sup.2 combinedly represent a phthaloyl group, with the exception of the case in which both P.sup.1 and P.sup.2 are simultaneously hydrogen atoms.) into contact with at least one microorganism selected from the group consisting of microorganisms belonging to the genera Candida, Geotrichum, Metschnikowia, Pachysolen, Pichia, Rhodotorula, Trichosporon, Zygosaccharomyces, Botryoascus, Cryptococcus, Citeromyces, Debaryomyces, Williopsis, Kloeckera, Lipomyces, Rhodosporidium, Saccharomycopsis and Wingea and capable of stereoselectively reducing said butanone derivative to the corresponding optically active 1-halo-3-amino-4-phenyl-2-butanol derivative of the general formula (2); ##STR2## (wherein X, R.sup.1, R.sup.2, P.sup.1 and P.sup.2 are as defined above.) and recovering the resulting optically active 1-halo-3-amino-4-phenyl-2-butanol derivative.
DETAILED DISCLOSURE OF THE INVENTION
In the following, the present invention is described in further detail.
The combinations of the substituents X, R.sup.1, R.sup.2, P.sup.1 and P.sup.2 in the (3S)-1-halo-3-amino-4-phenyl-2-butanone derivatives among the optically active 1-halo-3-amino-4-phenyl-2-butanone derivatives of the above general formula (1) to be used as the substrates in the production pr
REFERENCES:
patent: 4857468 (1989-08-01), Kutsuki et al.
patent: 5266485 (1993-11-01), Sawa et al.
Inoue Kenji
Sugawa Tadashi
Kaneka Corporation
Saucier Sandra E.
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