Claims
- 1. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR1## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR2## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (R)-form of said 2-hydroxy acid derivative of the formula (II) , wherein said microorganism is selected from the group consisting of:
- Sporidiobolus pararoseus;
- Rhodosporidium toruloides;
- Lactobacillus casei;
- Leuconostoc mesenteroides subsp. dextranicum; and
- Streptococcus equinus;
- and recovering the optically active (R)-2-hydroxy acid derivative of the formula (II) so produced.
- 2. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR3## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR4## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (S)-form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism is selected from the group consisting of:
- Lactobacillus plantarum;
- Ashbya gossypii;
- Serratia marcescens;
- Esherichia coli;
- Pseudomonas aureofaciens;
- Leuconostoc mesenteroides;
- Streptococcus faecalis;
- Sporolactobacillus inulinus;
- Candida rugosa;
- Pichia burtonii;
- Trigonopsis variabilis;
- Flavobacterium suaveolens; and
- Paracoccus denitrificans;
- and recovering the optically active (S)-2-hydroxy acid derivative of the formula (II) so produced.
- 3. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR5## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3, which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR6## wherein [X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,]X.sub.1, X.sub.2, R and n are as previously defined,
- with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (R) form of said 2-hydroxy acid derivative of the formula (II) , wherein said microorganism is selected from the group consisting of:
- ______________________________________Lactobacillus casei [IF012004] IFO 12004Leuconostoc mesenteroides [IF03349] IFO 3349subsp. dextranicumRhodosporidium toruloides [IF00559] IFO 0559[Saccharomyces rouxii IAM4011]______________________________________
- and recovering the optically active (R)-2-hydroxy acid derivative of the formula (II) so produced.
- 4. A process as in claim 3, wherein said 2-oxo acid derivative to be used as the starting material is selected from the group consisting of methyl, ethyl, propyl, and butyl esters of benzoylformic, phenylpyruvic, 2-oxo-4-phenylbutyric and 2-oxo-5-phenylvaleric acids.
- 5. A process as in claim 3, wherein said 2-oxo acid derivative used as the starting material is the ethyl ester of 2-oxo-4-phenylbutyric acid.
- 6. The process of claim 3, wherein said microorganism has been collected from the culture and resuspended in an aqueous medium prior to treating the said 2-oxo acid.
- 7. The process of claim 3, wherein said microorganism has been collected from the culture and the cells are ground, treated with acetone, or lyophilized prior to treating the said 2-oxo acid.
- 8. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR7## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula ( I ): ##STR8## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (S)-form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism is selected from the group consisting of:
- ______________________________________Lactobacillus plantarum [IF03070] IFO 3070Leuconostoc mesenteroides [AHU1067] AHU 1067Streptococcus faecalis [IF012964] IFO 12964Sporolactobacillus inulinus [NRIC1133] NRIC 1133[Candida pseudotropicalis IAM4829]Candida rugosa [IF00750] IFO 0750Pichia burtonii [IF01986] IFO 1986Trigonopsis variabilis [IF00755] IFO 0755Ashbya gossypii [IF01355] IFO 1355[Endomyces decipiens IF00102]Esherichia coli [IF03544] IFO 3544Serratia marcescens [IF03046] IFO 3046Pseudomonas aureofaciens [IF03522] IFO 3522 and[Brevibacterium ammoniagenes JAM1641]______________________________________
- and recovering the optically active (S)-2-hydroxy acid derivative of the formula (II) so produced.
- 9. A process as in claim 8, wherein said 2-oxo acid derivative to be used as the starting material is selected from the group consisting of methyl, ethyl, propyl, and butyl esters of benzoylformic, phenylpyruvic, 2-oxo-4-phenylbutyric and 2-oxo-5-phenylvaleric acids.
- 10. A process as in claim 8, wherein said 2-oxo acid derivative used as the starting material is the ethyl ester of 2-oxo-4-phenyl butyric acid.
- 11. The process of claim 8, wherein said microorganism has been collected from the culture and resuspended in an aqueous medium prior to treating the said 2-oxo acid.
- 12. The process of claim 8, wherein said microorganism has been collected from the culture and the cells ground, treated with acetone, or lyophilized prior to treating the said 2-oxo acid.
- 13. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR9## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR10## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (R)- form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism is selected from the group consisting of:
- ______________________________________Streptococcus equinus [NRIC1139] NRIC 1139Sporidiobolus pararoseus [AHU3447] AHU 3447Rhodosporidium toruloides [IF00559] IFO 0559 and[Saccharomyces rouxii IAM4011]______________________________________
- and recovering the optically active (R)-2-hydroxy acid derivative of the formula (II) so produced.
- 14. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR11## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR12## wherein X.sub.1, X.sub.2 , R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (S)-form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism is selected from the group consisting of:
- ______________________________________Streptococcus faecalis [IF012964] IFO 12964Sporolactobacillus inulinus [NRIC1133] NRIC 1133[Candida pseudotropicalis IAM4829]Candida rugosa [IF00750] IFO 0750Pichia burtonii [IF01986] IFO 1986Trigonopsis variabilis [IF00755] IFO 0755Ashbya gossypii [IF01355] lFO 1355[Endomyces decipiens IF00102]Esherichia coli [IF03544] IFO 3544Serratia marcescens [IF03046] IFO 3046Pseudomonas aureofaciens [IF03522] IFO 3522[Pseudomonas fluorescens IF03925][Brevibacterium ammoniagenes IAM1641]Flavobacterium suaveolens [IF03752] IFO 3752 andParacoccus denitrificans [IF012442] IFO 12442______________________________________
- and recovering the optically active (S)-2-hydroxy acid derivative of the formula (II) so produced.
- 15. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR13## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR14## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (R)-form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism is selected from the group consisting of:
- ______________________________________Lactobacillus casei [IF012004] IFO 12004subsp. caseiLeuconostoc mesenteroides [IF03349] IFO 3349subsp. dextranicumStreptococcus equinus [NRIC1139] NRIC 1139Sporidiobolus pararoseus [AHU3447] AHU 3447Rhodosporidium toruloides [IF00559] IFO 0559 and[Saccharomyces rouxii IAM4011]______________________________________
- and recovering the optically active (R)-2-hydroxy acid derivative of the formula (II) so produced.
- 16. The process of claim 15, wherein said microorganism has been collected from the culture and resuspended in an aqueous medium prior to treating the said 2-oxo acid.
- 17. The process of claim 15, wherein said microorganism has been collected from the culture and the cells ground, treated with acetone, or lyophilized prior to treating the said 2-oxo acid.
- 18. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR15## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR16## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (S)-form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism is selected from the group consisting of:
- ______________________________________Lactobacillus plantarum [IF03070] IFO 3070Streptococcus faecalis [IF012964] IFO 12964Sporolactobacillus inulinus [NRIC1133] NRIC 1133Candida rugosa [IF00750] IFO 0750Pichia burtonii [IF01986] IFO 1986Ashbya gossypii [IF01355] IFO 1355[Endomyces decipiens IF00102]Esherichia coli [IF03544] IFO 3544Serratia marcescens [IF03046] IFO 3046Pseudomonas aureofaciens [IF03522] IFO 3522[Bacillus subtilis IF03007][Brevibacterium ammoniagenes [IAM1641]Flavobacterium suaveolens [IF03752] IFO 3572 andParacoccus denitrificans [IF012442] IFO 12442______________________________________
- and recovering the optically active (S)-2-hydroxy acid derivative of the formula (II) so produced.
- 19. The process of claim 16, wherein said microorganism has been collected from the culture and resuspended in an aqueous medium prior to treating the said 2-oxo acid.
- 20. The process of claim 18, wherein said microorganism has been collected from the culture and the cells ground, treated with acetone, or lyophilized prior to treating the said 2-oxo acid.
- 21. A process for the production of an optically active 2 -hydroxy acid derivative represented by the formula (II): ##STR17## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR18## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (R)-form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism is selected from the group consisting of:
- ______________________________________Sporidiobolus pararoseus [AHU3447] AHU 3447Rhodosporidium toruloides [IF00559] IFO 0559[Saccharomyces rouxii IAM4011]Lactobacillus casei [IF012004] lFO 12004Leuconostoc mesenteroides [IF03349] IFO 3349 andsubsp. dextranicumStreptococcus equinus [NRIC1139] NRIC 1139and recovering the optically active (R)-2-hydroxy acidderivative of the formula (II) so produced.______________________________________
- and recovering the optically active (R)-2-hydroxy acid derivative of the formula (II) so produced.
- 22. The process of claim 21, wherein said microorganism has been collected from the culture and resuspended in an aqueous medium prior to treating the said 2-oxo acid.
- 23. The process of claim 21, wherein said microorganism has been collected from the culture and the cells ground, treated with acetone, or lyophilized prior to treating the said 2-oxo acid.
- 24. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR19## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR20## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (S)-form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism is selected from the group consisting of:
- ______________________________________Lactobacillus plantarum [IF03070] IFO 3070Ashbya gossypii [IF01355] IFO 1355[Endomyces decipiens IF00102]Serratia marcescens [IF03046] IFO 3046Esherichia coli [IF03544] IFO 3544Pseudomonas aureofaciens [IF03522] IFO 3522Leuconostoc mesenteroides [AHU1067] AHU 1067Streptococcus faecalis [IF012964] IFO 12964Sporolactobacillus inulinus [NRIC1133] NRIC 1133[Candida pseudotropicalis IAM4829]Candida rugosa [IF00750] IFO 0750Pichia burtonii [IF01986] IFO 1986Trigonopsis variabilis [IF00755] IFO 0755[Bacillus subtilis IF03007][Brevibacterium ammoniagenes IAM1641]Flavobacterium suaveolens [IF03752] IFO 3752 andParacoccus denitrificans [IF012442] IFO 12442______________________________________
- and recovering the optically active (S)-2-hydroxy acid derivative of the formula (II) so produced.
- 25. The process of claim 24, wherein said microorganism has been collected from the culture and resuspended in an aqueous medium prior to treating the said 2-oxo acid.
- 26. The process of claim 24, wherein said microorganism has been collected from the culture and the cells ground, treated with acetone, or lyophilized prior to treating the said 2-oxo acid.
- 27. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR21## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR22## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (R)-form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism has all of the identifying characteristics of a microorganism selected from the group consisting of:
- ______________________________________Lactobacillus casei IFO 12004;subsp. caseiLeuconostoc mesenteroides IFO 3349;subsp. dextranicumStreptococcus equinus NRIC 1139;Sporidiobolus pararoseus AHU 3447; andRhodosporidium toruloides IFO 0559;______________________________________
- and recovering the optically active (R)-2-hydroxy acid derivative of the formula (II) so produced.
- 28. A process for the production of an optically active 2-hydroxy acid derivative represented by the formula (II): ##STR23## wherein X.sub.1 and X.sub.2 represent each a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group or an alkyl group, R represents an alkyl or a phenyl group, and n is an integer ranging from 0 to 3,
- which comprises treating a 2-oxo acid derivative represented by the formula (I): ##STR24## wherein X.sub.1, X.sub.2, R and n are as previously defined, with a microorganism capable of asymmetrically reducing said 2-oxo acid derivative of the formula (I) into an optically active (S)-form of said 2-hydroxy acid derivative of the formula (II), wherein said microorganism has all of the identifying characteristics of a microorganism selected from the group consisting of:
- ______________________________________Trigonopsis variabilis IFO 0755Lactobacillus plantarum IFO 3070;Streptococcus faecalis IFO 12964;Sporolactobacillus inulinus NRIC 1133;Candida rugosa IFO 0750;Pichia burtonii IFO 1986;Ashbya gossypii IFO 1355;Eserichia coli IFO 3544;Serratia marcescens IFO 3046;Pseudomonas aureofaciens IFO 3522;Leuconostoc mesenteroides AHU 1067Flavobacterium suaveolens IFO 3572; andParacoccus denitrificans IFO 12442;______________________________________
- and recovering the optically active (S)-2-hydroxy acid derivative of the formula (II) so produced.
Priority Claims (4)
Number |
Date |
Country |
Kind |
63-30476 |
Feb 1988 |
JPX |
|
63-30477 |
Feb 1988 |
JPX |
|
63-105892 |
Apr 1988 |
JPX |
|
63-109938 |
Apr 1988 |
JPX |
|
Parent Case Info
This application is a continuation, of application Ser. No. 07/819,679 filed on Jan. 13, 1992, now abandoned, which is a continuation application of Ser. No. 07/415,325, filed on Sep. 21, 1989, now abandoned.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
4609623 |
Leuchtenberger et al. |
Sep 1986 |
|
4785089 |
Blaser et al. |
Nov 1988 |
|
5098841 |
Ghisalba et al. |
Mar 1992 |
|
5256552 |
Matsuyama et al. |
Oct 1993 |
|
Non-Patent Literature Citations (2)
Entry |
Deol et al., Aust. J. Chem., 29(11), pp. 2459-2467, 1976. |
ATCC Catalogue of Fungi/Yeasts, 17th edition, pp. 324 and 346-347, 1987. |
Continuations (2)
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Number |
Date |
Country |
Parent |
819679 |
Jan 1992 |
|
Parent |
415325 |
Sep 1989 |
|