Process for the production of optically active 2-hydroxy-4-pheny

Details Process for the production of optically active 2-hydroxy-4-pheny Process for the production of optically active 2-hydroxy-4-pheny

1990-03-01

1993-03-16

Lilling, Herbert J.

Chemistry: molecular biology and microbiology

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

Preparing oxygen-containing organic compound

435280, 435822, 435824, 435830, 435836, 435840, 435843, 435850, 435852, 435853, 435857, 435873, 435874, 435885, 435911, 435921, 435930, C12P 742, C12R 122, C12R 101, C12R 1645

Patent

active

051943808

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

This invention relates to a process for the production of optically active 2-hydroxy-4-phenyl-3-butenoic acid. More particularly, it relates to a process for the production of optically active 2-hydroxy-4-phenyl-3-butenoic acid which comprises treating 2-oxo-4-phenyl-3-butenoic acid with an optionally treated microorganism capable of asymmetrically reducing the 2-oxo-4-phenyl-3-butenoic acid into (R)-2-hydroxy-4-phenyl-3-butenoic acid or (S)-2-hydroxy-4-phenyl-3-butenoic acid, and collecting the (R)-2-hydroxy-4-phenyl-3-butenoic acid or (S)-2-hydroxy-4-phenyl-3-butenoic acid thus formed.
Optically active 2-hydroxy-4-phenyl-3-butenoic acid is an important intermediate in the production of various drugs, optically active and physiologically active substances, and derivatives thereof.
Further, optically active 2-hydroxy-4-phenylbutyric acid, which is an important intermediate in the production of drugs such as ACE inhibitors, can be readily obtained by bringing optically active 2-hydroxy-4-phenyl-3-butenoic acid into contact with a hydrogenation catalyst such as palladium in a hydrogen atmosphere.


PRIOR ART

Known methods for the production of optically active 2-hydroxy-4-phenyl-3-butenoic acid include one which comprises treating a racemic mixture of said acid with bornylamine to thereby form diastereomers and then optically resolving the same [cf. Chem. Ber., 89, 671-677 (1956)], and another one comprising optical resolution through liquid chromatography with the use of a packing comprising a carrier containing a metal salt of an optically active amino acid bound thereto (cf. Japanese Patent Laid-Open No. 87640/1986). However, the former method requires a complicated procedure, which makes it undesirable from an industrial viewpoint. On the other hand, the latter method is disadvantageous from an economic viewpoint. Thus, it has been necessary to develop a simple and economical method therefor. In addition, no process has been described for the production of optically active 2-hydroxy-4-phenyl-3-butenoic acid from 2-oxo-4-phenyl-3-butenoic acid by using a microorganism capable of asymmetrically reducing the 2-oxo-4-phenyl-3-butenoic acid.


DISCLOSURE OF THE INVENTION

The present inventors have developed asymmetric reduction with a microorganism as a process for readily producing optically active 2-hydroxy-4-phenyl-3-butenoic acid of high optical purity, and attempted to discover microorganisms suitable for this purpose. As a result, they have determined that a microorganism belonging to the genus Lactobacillus, Leuconostoc, Streptococcus, Sporolactobacillus, Pediococcus, Arthrobacter, Agrobacterium, Ambrosiozyma, Achromobacter, Arthroascus, Aureobacterium, Bacillus, Botryoascus, Brevibacterium, Candida, Clavispora, Corynebacterium, Flavobacterium, Geotrichum, Hansenula, Kluyveromyces, Lipomyces, Lodderomyces, Proteus, Pseudomonas, Saccharomycopsis, Schizosaccharomyces, Stephanoascus, Torulaspora, Trigonopsis, Wickerhamiella, Enterobacter, Klebsiella or Xanthomonas can asymmetrically reduce 2-oxo-4-phenyl-3-butenoic acid to thereby give (R)-2-hydroxy-4-phenyl-3-butenoic acid, and that a microorganism belonging to the genus Lactobacillus, Leuconostoc or Streptococcus can asymmetrically reduce 2-oxo-4-phenyl-3-butenoic acid to thereby give (S)-2-hydroxy-4-phenyl-3-butenoic acid, thus completing the present invention.
In the present invention, therefore, any microorganism belonging to the genus Lactobacillus, Leuconostoc, Streptococcus, Sporolactobacillus, Pediococcus, Arthrobacter, Agrobacterium, Ambrosiozyma, Achromobacter, Arthroascus, Aureobacterium, Bacillus, Botryoascus, Brevibacterium, Candida, Clavispora, Corynebacterium, Flavobacterium, Geotrichum, Hansenula, Kluyveromyces, Lipomyces, Lodderomyces, Proteus, Pseudomonas, Saccharomycopsis, Schizosaccharomyces, Stephanoascus, Torulaspora, Trigonopsis, Wickerhamiella, Enterobacter, Klebsiella or Xanthomonas and capable of asymmetrically reducing 2-oxo-4-phenyl-3-butenoic acid to thereby give (R)-2-hydroxy-4-phenyl-3-butenoi

REFERENCES:
Biotech Abs 85-12678 (J60156394) Aug. 1985.
Biotech Abs 90-05694 (J02016987) Jan. 1990.
Biotech Abs 89-14981 (WO8907147) Aug. 1989.
Biotech Abs 90-03378 (EP-347374) Dec. 1989.
Nerdel et al. (1956) Chem. Ber., 89:671-677.

Affiliated with

Also associated with

Rating

Process for the production of optically active 2-hydroxy-4-pheny does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the production of optically active 2-hydroxy-4-pheny, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the production of optically active 2-hydroxy-4-pheny will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-350408