Process for the biotechnological preparation of L-thienylalanine

Details Process for the biotechnological preparation of L-thienylalanine Process for the biotechnological preparation of L-thienylalanine

1995-06-05

1998-07-14

Mullis, Jeffrey C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549 29, 549 81, C07D23910, C07D23364, C07D33304

Patent

active

057806403

ABSTRACT:
Process for the biotechnological preparation of L-thienylalanines in enantiomerically pure form from 2-hydroxy-3-thienylacrylic acids, and their use.
L-Thienylalanines are prepared via the hydantoin or the azlactone route. The starting substances used for the biotransformation are 2-hydroxy-3-thienylacrylic acids. The innovative step consists in the transamination of the enol form of the 2-hydroxy-3-thienylacrylic acids to give L-thienylalanines with the aid of biotransformation. The transaminiation is carried out in the presence of L-aspartic acid or L-glutamic acid as amino donor.

REFERENCES:
patent: 3971700 (1976-07-01), Roesten
Enzyme Nomenclature, pp. 220, 222 (1984).
Hruban et al. "Effects of Some Phenylalanine Analogs upon Protein Metabolism in Vivo", Laboratory Investigation 14(5) 1965.
EPO Search Report for EP 93 11 2006, Dec. 4, 1994.
Bladon, C.M., "Synthesis of Heteroaromatic Thyrotropin-releasing Hormone Analogues," J. Chem. Soc. Perkin Trans 1:1151-58 (1990).
Cooper, A.J.L., et al., "Synthesis and Properties of the .alpha.-Keto Acids," Chem. Rev. 83:321-58 (1983).
Horner, L., et al., ".alpha.-Methoxy-, .alpha.-Athylmercapto-und .alpha.-Dimethylamino-acrylester aus Substituierten Essigestern mit Aldehyden," Liebigs Ann. Chem. 703:37-43 (1967).
Sheldon, R.A., et al., "the Synthesis of Angiotensin-Converting Enzyme (ACE) Inhibitors," Chimicaoggi 35-47 (May 1991).
Chibata, I., et al., "Use of Immobilized Cells," Ann. Rev. Biophys. Bioeng. 10:197-216 (1981).
Syldatk, C., et al., "Production of Optically Pure D-and L-.alpha.-Amino Acids by Bioconversion of D,L-5-Monosubstituted Hydantoin Derivatives," Advances in Biochem. Eng./Biotech. 41:29-75 (1990).
Moller, A., et al., "Stereo-and Substrate-Specificity of a D-Hydantoinase and a D-N-carbamyl-amino Acid Amidohydrolase of Arthrobacter crystallopoietes AM 2," Enzyme Microb. Tech. 10:618-25 (1988).
Wichmann, R., et al., "Continuous Microbial Production of L-leucine with Cell Retention," Appl. Microbiol. Biotech. 32:373-79 (1990).
Ng, S.C., et al., "Simple Purification Procedure for L-.alpha.-Amino Acids Generated by Enzymatic Transamination of .alpha.-Keto Acids from the L-Glutamic Acid Amino Donor," Bull Sing. N.I. Chem. 18:127-29 (1990).
Lipkowski, A.W., et al., "Resolution of .beta.-2-Thienylalanine Enantiomers by a Convenient Method," Polish J. of Chem. 54:2225-28 (1981).
Pugniere, M., et al., "A Recirculating Packed-Bed Reactor for Enzyme Catalysed Reactions in Two Liquid-Phase System," Biotech. Techniques 3(5):339-44 (1989).
Scott, T., et al., Concise Encyclopedia Biochemistry 1, 75-82 (2d ed. 1988).
Lipkowski, A.W., "Resolution of t-Butyloxycarbonyl-.alpha.-Phenylglycine Enantiomers by a Convenient Method," Polish Journal of Chemistry 55:1725-27 (1981).
Tan et al. "Synthesis and Study of S-furylmethylenehydrations . . . ", J. Phys. Org. Chem., 4(11), 681-8, 1991.
Meanwell et al. ". . . Preparation of C-5 Unsturated Hydantoin Derivatives", J. Org. Chem. 56, 6897-6904, 1991.

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