Processes for production of optically active 3-phenyl-1,3-propanediol by asymmetric assimilation

• US 5,356,812 A
• Filed: 04/07/1992
• Issued: 10/18/1994
• Est. Priority Date: 08/10/1990
• Status: Expired due to Fees

• Current Assignee: Daicel Chemical Industries Limited
• Original Assignee: Daicel Chemical Industries Limited
• Inventors: Kobayashi, Yoshinori, Ito, Michio, Matsuyama, Akinobu, Kawada, Naoki
• Primary Examiner(s): Marx, Irene
• Assistant Examiner(s): SAUCIER, SANDRA E
• Application Number:
  US07/844,609
• Time in Patent Office: 924 Days
• Field of Search: 435/280, 435/822, 435/911
• US Class Current: 435/280
• CPC Class Codes: C12P 41/001 by metabolizing one of the enantiomers
• CPC Class Codes: C12P 7/22 aromatic
• CPC Class Codes: Y10S 435/822 using bacteria or actinomycetales
• CPC Class Codes: Y10S 435/911 using fungi

Abstract

A microorganism or a preparation thereof is permitted to act on a mixture of enantiomers of 3-phenyl-1, 3-propanediol, and the residual optically active 3-phenyl-1,3-propanediol is harvested.

The genera of those microorganisms which are able to leave (R)-3-phenyl-1,3-propanediol include Candida, Hansenula, Rhodotorula, Protaminobacter, Aspergillus, Alternaria, Macrophomina, Preussia and Talaromyces.

The genera of those microorganisms which are able to leave (S)-3-phenyl-1,3-propanediol include Candida, Geotrichum, Leucosporidium, Pichia, Torulaspora, Trichosporon, Escherichia, Micrococcus, Corynebacterium, Gordona, Rhodococcus, Aspergillus, Emericella, Absidia, Fusarium, Dactylium, Serratia and Pseudomonas.

Claims

1. A process for increasing the optical purity of (R)-3-phenyl-1,3-propanediol comprising:

providing a mixture of (R) and (S) enantiomers of 3-phenyl-1,3-propanediol,

subjecting said mixture to a microorganism selected from the group consisting of Candida lambica, Hanesnula minuta, Rhodotorula rubra, Protaminobacter ruber, Aspergillus niger, Aspergillus ficuum, Alternaria kiduchiana, Macrophomina phaseoli, Preussia terricola, and Talaromyces flavus var. flavus, or a preparatus derived therefrom, that is capable of selectively utilizing the (S)-3-phenyl-1,3-propanediol enantiomer, and

recovering the residual, optically active 3-phenyl-1,3-propanediol.

2. The process for increasing the optical purity of (R)-3-phenyl-1,3-propanediol according to claim 1, wherein the microorganism is selected from the group consisting of Candida lambica DSM 70090, Hansenula minuta DSM 70274, Rhodotorula rubra AHU 3945 or AHU 3948, Protaminobacter ruber IAM 1081, Aspergillus niger IFO 4414, Aspergillus ficuum IFO 4318, Alternaria kikuchiana IFO 5778, Macrophomina phaseoli IFO 6696, Preussia terricola IFO 7893, and Talaromyces flavus var. flavus IFO 7231.

3. The process for increasing the optical purity of (R)-3-phenyl-1,3-propanediol according to claim 1, wherein said mixture is racemic 3-phenyl-1,3-propanediol.

4. The process for increasing the optical purity of (R)-3-phenyl-1,3-propanediol according to claim 1, wherein said microorganism is grown in a fluid medium, and said mixture of enantiomers of 3-phenyl-1,3-propanediol is added to a cell dispersion of the microorganism.

5. The process for increasing the optical purity of (R)-3-phenyl-1,3-propanediol according to claim 1, wherein said mixture is subjected to said microorganism or preparation thereof at a pH of from about 3 to about 10 and a temperature of from about 10°

C. to about 60°

C.

6. The process for increasing the optical purity of (R)-3-phenyl-1,3-propanediol according to claim 1, wherein the concentration of said mixture of enantiomers is from about 0.1 to about 20 percent by weight.

7. A process for increasing the optical purity of (S)-3-phenyl-1,3-propanediol comprising:

providing a mixture of (R) and (S) enantiomers of 3-phenyl-1,3-propanediol,

subjecting said mixture to a microorganism selected from the group consisting of Candida pintolopesii var. pintolopesii, Geotrichum candidum, Geotrichum fermentans, Geotrichum klebahnii, Leucosporidium scottii, Pichia quercum, Torulaspora delbrueckii, Trichosporon capitarum, Escherichia coli, Micrococcus luteus, Corynebacterium hoagii, Gordona rubro, Rhodococcus equi, Rhodococcus sp. JCM 6832, Rhodococcus marls, Rhodococcus fascians, Rhodococcus erythropolis, Rhodococcus rhodochrous, Rhodococcus coprophilus, Rhodococcus terrae, Aspergillus niger, Aspergillus ficuum, Emeticella midulans, Absidia coerulea, Fusarium solani, Dactylium dendriodes, Serratia sp. No. 2664 (FERM BP-4319), Serratia sp. No. 2666 (FERM BP-4320), and Pseudomonas putida, or a preparation derived therefrom, that is capable of selectively utilizing the (R)-3-phenyl-1,3-propanediol enantiomer, and

recovering the residual, optically active 3-phenyl-1,3-propanediol.

8. The process for increasing the optical purity of (S) -3-phenyl-1,3-propanediol according to claim 7, wherein the microorganism is selected from the group consisting of Candida pintolopesii var. pintolopesii IFO 0729, Geotrichum candidum IFO 4597, IFO 4598, IFO 5368, IFO 31810, JCM 1747 or JCM 5222, Geotrichum fermentans JCM 2467 or JCM 2468, Geotrichum klebahnii JCM 2171, Leucosporidium scottii IFO 1923, Pichia quercuum DSM 70386, Torulaspora delbrueckii IFO 0955, Trichosporon capitaturn IFO 1197, Escherichia coli IFO 3543, Micrococcus luteus IFO 12708, Corynebacterium hoagii JCM 1319, Gordona rubro JCM 3199, Rhodococcus equi JCM 6820, Rhodococcus sp. JCM 6832, Rhodococcus maris JCM 6167, Rhodococcus fascians JCM 1316, Rhodococcus erythropolis IFO 12540, Rhodococcus rhodochrous DSM 43008, Rhodococcus coprophilus DSM 43302, Rhodococcus terrae DSM 43342, Aspergillus niger IFO 4415, Aspergillus ficuum IFO 4320, Emeticella midulans IAM 2086, Absidia coerulea JCM 5598, Fusarium solani IFO 5232, Dactylium dendroides ATCC 46032, Serratia sp. No. 2664 (FERM BP-4319), Serratia sp. No. 2666 (FERM BP-4320) and Pseudomonas putida No. 2145B (FERM BP-4321).

9. The process for increasing the optical purity of (S)-3-phenyl-1,3-propanediol according to claim 7, wherein said mixture is racemic 3-phenyl-1,3-propanediol.

10. The process for increasing the optical purity of (S)-3-phenyl-1,3-propanediol according to claim 7, wherein said microorganism is grown in a fluid medium, and said mixture of enantiomers of 3-phenyl-1,3-propanediol is added to a cell dispersion of the microorganism.

11. The process for increasing the optical purity of (S)-3-phenyl-1,3-propanediol according to claim 7, wherein said mixture is subjected to said microorganism or preparation thereof at a pH of from about 3 to about 10 and a temperature of from about 10°

C. to 60°

C.

12. The process for increasing the optical purity of (S)-3-phenyl-1,3-propanediol according to claim 7, wherein the concentration of said mixture of enantiomers is from about 0.1 to about 20 percent by weight.