Method of producing (R)-2-amino-1-phenylethanol and optically ac

Details Method of producing (R)-2-amino-1-phenylethanol and optically ac Method of producing (R)-2-amino-1-phenylethanol and optically ac

1996-08-29

1998-03-24

Saucier, Sandra E.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing nitrogen-containing organic compound

435280, 435106, C12P 1304, C12P 1300

Patent

active

057311757

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to a method of producing (R)-2-amino-1-phenylethanol or its halogen substitution products, and optically active phenylserine and its halogen substitution products, which are represented by Formula (2), using an enzyme or microorganism. The present invention also relates to a chemical compound 3-(3-chlorophenyl)serine, which is a substrate of the reaction of the enzyme or microorganism. (R)-2-amino-1-phenylethanol and its halogen substitution products, represented by Formula (2), are industrially useful as raw materials of medical or agricultural chemicals, especially anti-obesity drugs. The optically active phenylserine and its halogen substitution products are useful as raw materials for medicines, especially antibiotics. ##STR1## X is H, F, Cl, Br, or I, and may be located at any of the ortho, recta, and para positions.


BACKGROUND OF THE INVENTION

There have conventionally been several methods for producing (R)-2-amino-1-phenylethanol or its halogen substitution products, represented by Formula (2). The following methods for producing optically active 2-amino-1-phenylethanol or its halogen substitution products are known: (1992)); using LiAlH.sub.4 (Synthesis, (7), 575-578 (1990)); and then aminating the product (Indian J. Chem., Sect. B, 31B(12), 821-823 (1992)); Publication No. Sho 61-85197); Kagaku Kaishi (5), 910-913 (1985)); borane to obtain the R form (J. Org. Chem., 50, 3237-3239 (1985)); phosphine substituting an alkali metal sulfonate (Japanese Patent Laid-Open Publication No. Hei 5-170780).
The following method for producing (R)-2-amino-1-(3-chlorophenyl)ethanol is the only method known: racemic 2-amino-1-(3-chlorophenyl)ethanol, forming a salt of diasteroisomers, and then optically resolving the salt by means of preferentially crystallizing a salt of (R)-2-amino-1-(3-chlorophenyl)ethanol and N-(t-butoxycarbonyl)-D-alanine (European Patent Laid-Open Publication No. 294995).
The following methods for producing optically active phenylserine and its halogen substitution products are known: (Angew. Chem., 106 (1), 106-108 1994)); racemate with aldolase and leaving an enantiomer (Japanese Patent Laid-Open Publications No. Hei 6-165693 and No. Hei 6-125786; Japanese Patent Publication No. Sho 52-46313; Can. J. Chem., 72 (1), 114-117 (1994)); and (S)-alanine, a pyridoxal derivative, and Cu(II) (Chem. Lett., (1), 55-58 (1994)); acylase (Bioorg. Khim., 19 (4), 478-483 (1993)); (1992)); N-bromosuccinimide, and then reacting with AgNO.sub.3 (Tetrahedron Lett., 31 (48), 7059-7062 (1990)); of an optically active ferrocene and a gold complex to form an optically active oxazoline, and then hydrolyzing the optically active oxazoline (Japanese Patent Laid-Open Publication No. Sho 63-60977); glycine (J. Chem. Soc. Perkin Trans. 1 (24), 3143-3155 (1993)).
With regard to 3-(3-chlorophenyl) serine, a substrate of the reaction used in the present invention, its erythro form has been reported (R. J. Ulevitch and R. G. Kallen, Biochemistry, 16 (24), 5355-5363 (1977)), but no detailed synthesizing method is described.
The conventional methods for producing (R)-2-amino-1-phenylethanol or its halogen substitution products, have the following problems: is not easy, and the yield is not high. high concentration of 10,000 U/l. the microbial reaction is very small, resulting in high cost. crystals obtained in one batch is small, which is not economical. not sufficiently high. recovering method, which precludes it from industrial use. economical production of (R)-2-amino-1-phenylethanol and its halogen substitution products, represented by Formula (2). Therefore, there is a desire to develop a method for producing (R)-2-amino-1-phenylethanol and its halogen substitution products, which can be industrially employed.
The conventional methods for producing optically active phenylserine and its halogen substitution products, have the following problems:
In Methods (9), (11), (15), and (16), a large mount of an optically active catalyst needs to be synthesized. Difficulty an

REFERENCES:
patent: 3930948 (1976-01-01), Sano et al.
Ulevitch et al., "Studies of the Reactions of Substituted D,L-erythro-beta-Phenylserines with Lamb Liver Serine Hydroxymethylase. Effects of Substituents upon the Dealdolization Step", Biochemistry 16 (24):5355-5363 (1977).
TomodaT. et al., B. Osaka Med. Sch. 12(1):5-9 (1966).

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