Chemistry: molecular biology and microbiology – Enzyme – proenzyme; compositions thereof; process for... – Hydrolase
Patent
1992-06-02
1994-12-13
Robinson, Douglas W.
Chemistry: molecular biology and microbiology
Enzyme , proenzyme; compositions thereof; process for...
Hydrolase
435123, 435280, 4352565, 435126, C12P 1702, C12N 914
Patent
active
053729404
DESCRIPTION:
BRIEF SUMMARY
FIELD OF INDUSTRIAL APPLICATION
D-pantolactone is known as an intermediate in the preparation of D-pantothenic acid and pantethine. Both are useful as vitamins of medical or physiological importance.
The present invention relates to a new enzyme useful for the optical resolution of D,L-pantolactone and a process for the preparation thereof.
BACKGROUND ART
D-pantolactone has heretofore been prepared through optical resolution of chemically synthesized D,L-pantolactone.
Such process, however, requires the use of costly resolving agents such as quinine or brucine, and suffers from the drawback that the recovery of D-pantolactone is not easy.
Processes of optical resolution of D,L-pantolactone by enzymatic asymmetric hydrolysis have also been known from Japanese published unexamined patent application No. 57-52895 (JP, A, 57-152895) and Japanese published unexamined patent application No. 62-294092 (JP, A, 62-294092). In these processes, the L-pantolactone in D,L-pantolactone is selectively subjected to asymmetric hydrolysis using microorganisms to afford D-pantolactone. These processes have the disadvantage that L-pantolactone, not being completely hydrolysable, does not yield D-pantolactone of high optical purity, and they are also of little significance as practical processes for the preparation of D-pantolactone due to the fact that both the substrate concentration and the reaction rate are low.
As a result of extensive research on the asymmetric hydrolysis of D,L-pantolactone, the present inventors have previously found that D-pantolactone can be obtained efficiently from D,L-pantolactone through selective asymmetric hydrolysis by certain microorganisms of the D-pantolactone only in D,L-pantolactone to form D-pantoic acid, followed by separation, and conversion into D-pantolactone of the D-pantoic acid (see Japanese patent application No. 1-200347).
Thus, the present inventors have succeeded in providing a process for the preparation of D-pantolactone, characterized in that the D-pantolactone in D,L-pantolactone is selectively subjected to asymmetric hydrolysis using a microorganism possessing lactone-hydrolyzing ability selected from microorganisms belonging to the genera Fusarium, Cylndrocarpon, Gibbrella, Aspergillus, Penicillium, Rhizopus, Volutella, Gliocladium, Eurotium, Nectria, Schizophyllum, Myrothecium, Neurospora, Acremonium, Tuberculina, Absidia, Sporothrix, Verticillium or Arthroderma, to form D-pantoic acid, which is then separated and converted into D-pantolactone. The invention has many advantages over the above-mentioned known processes of selective asymmetric hydrolysis of the L-pantolactone in D,L-pantolactone, for example in that considerably higher substrate concentrations may be used, that shorter reaction times may be employed, and that D-pantolactone of extremely high optical purity can be obtained.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 shows the activity vs. pH relationship;
FIG. 2 shows the activity vs. temperature relationship;
FIG. 3 shows the activity vs. pH relationship, as determined by treatment at 30 C for 60 minutes at different pH's;
FIG. 4 shows the activity vs. temperature relationship, as determined by treatment at pH 7.0 for 60 minutes at different temperatures, of D-pantolactone hydrolase of the present invention.
DISCLOSURE OF THE INVENTION
The present inventors have now succeeded in obtaining a new enzyme capable of specifically hydrolyzing D-lactone from the specific microorganisms used in the present inventors' process mentioned above for the selective asymmetric hydrolysis of the D-pantolactone only in D,L-pantolactone. Thus, the present inventors have succeeded in obtaining a new D-pantolactone hydrolase from the culture broth to a microorganism with the ability of produce said new enzyme capable of specifically hydrolyzing D-pantolactone, selected from microorganisms belonging to the genera Fusarium, Cylindrocarpon, Gibberella, Asperillus, Penicillium, Rhizopus, Volutella, Gliocladium, Eurotium, Nectria, Schizophyllum, Myrothecium, Neurospora, Ac
REFERENCES:
patent: 3850750 (1974-11-01), Lanzioletta
patent: 5084392 (1992-01-01), Miyazawa et al.
Japanese Unexamined Patent Application Publication No. JP, A, 62-294092.
Japanese Unexamined Patent Application Publication No. JP, A, 57-1528-95.
Japanese Unexamined Patent Application Publication No. JP, B1 47-19745.
Japanese Unexamined Patent Application Publication No. JP, A,3-65198.
Derwent Biotechnology Abstract AN:. 90-10004.
Derwent Biotechnology Abstract AN: 88-04298.
Derwent Abstract AN: 85-287881.
Canadian Patent Application 2,037,043.
Takashi et al. (1989), Journal of Chromatography 474, pp. 405-410.
Sakamoto Keiji
Shimizu Sakayu
Yamada Hideaki
Fuji Yakuhin Kogyo Kabushiki Kaisha
Robinson Douglas W.
Sevigny Jeffrey J.
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