Synthesis of l-homophenylalanine via integrated membrane bioreactor: Influence of pH on yield

Biochemical Engineering Journal

Volumn 52, Issue 2-3, 2010, Pages 296-300

  Ahmad, A L ^a   Oh, P C ^a   Shukor, S R A ^a  

^a SCHOOL OF PHYSICS   (Malaysia)

Author keywords

Biocatalysis; Biotransformation; L homophenylalanine; Membrane bioreactor; PH; Reductive amination

Indexed keywords

BIOCATALYSIS; BIOTRANSFORMATION; L-HOMOPHENYLALANINE; MEMBRANE BIOREACTOR; REDUCTIVE AMINATION;

AMINES; AMINO ACIDS; ATMOSPHERIC PRESSURE; BIOCONVERSION; DIALYSIS; ENZYMES; MEMBRANES; SYNTHESIS (CHEMICAL);

BIOREACTORS;

DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; FORMATE DEHYDROGENASE; HOMOPHENYLALANINE; OXIDOREDUCTASE; PHENYLALANINE; PHENYLALANINE DEHYDROGENASE; UNCLASSIFIED DRUG;

AMINATION; AMINO ACID SYNTHESIS; ARTICLE; BIOCATALYSIS; BIOREACTOR; BIOTRANSFORMATION; ENZYME ACTIVITY; PH; PRIORITY JOURNAL; RECYCLING; REDUCTION;

EID: 77957943041     PISSN: 1369703X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bej.2010.08.010     Document Type: Article

References (24)

1. Liese A., Kragl U., Kierkels H., Schulze B. Membrane reactor development for the kinetic resolution of ethyl 2-hydroxy-4-phenylbutyrate. Enzyme Microb. Technol. 2002, 30:673-681.
2. Trevor A.J., Katzung B.G., Masters S.B. Katzung & Trevor's Pharmacology 2002, McGraw-Hill Companies, Inc, New York.
3. Ondetti M.A., Cushman D.W. Inhibition of the renin-angiotensin system: a new approach to the therapy of hypertension. J. Med. Chem. 1981, 24:355-361.
4. Liese A., Seelbach K., Wandrey C. Industrial Biotransformations 2000, Wiley-VCH Verlag GmbH, Weinheim.
5. Johnson A.L., Price W.A., Wong P.C., Vavala R.F., Stump J.M. Synthesis and pharmacology of the potent angiotensin-converting enzyme-inhibitor N-[1(S)-(ethoxycarbonyl)-3-phenylprophyl]-(S)-alanyl-(S)-pyroglutamic acid. J. Med. Chem. 1985, 28:1596-1602.
6. Larissegger-Schnell B., Glueck S.M., Kroutil W., Faber K. Enantio-complementary deracemization of (+/-)-2-hydroxy-4-phenylbutanoic acid and (+/-)-3-phenyllactic acid using lipase-catalyzed kinetic resolution combined with biocatalytic racemization. Tetrahedron 2006, 62:2912-2916.
7. Bai Y.L., Yang S.T. Biotransformation of R-2-hydroxy-4-phenylbutyric acid by d-lactate dehydrogenase and Candida boidinii cells containing formate dehydrogenase coimmobilized in a fibrous bed bioreactor. Biotechnol. Bioeng. 2005, 92:137-146.
8. Ahmad A.L., Oh P.C., Shukor S.R.A. Sustainable biocatalytic synthesis of l-homophenylalanine as pharmaceutical drug precursor. Biotechnol. Adv. 2009, 27:286-296.
9. Yen M.C., Hsu W.H., Lin S.C. Synthesis of l-homophenylalanine with immobilized enzymes. Process Biochem. 2010, 45:667-674.
10. Cho B.K., Seo J.H., Kang T.W., Kim B.G. Asymmetric synthesis of l-homophenylalanine by equilibrium-shift using recombinant aromatic l-amino acid transaminase. Biotechnol. Bioeng. 2003, 83:226-234.
11. Wu W.N., McKown L.A. Recent advances in biotransformation of CNS and cardiovascular agents. Curr. Drug Metab. 2000, 1:255-270.
12. Ahuja S. Chiral Separations: Application and Technology 1997, American Chemical Society, Washington.
13. Patel R.N., Goswami A., Chu L., Donovan M.J., Nanduri V., Goldberg S., Johnston R., Siva P.J., Nielsen B., Fan J.Y., He W.X., Shi Z.P., Wang K.W., Eiring R., Cazzulino D., Singh A., Mueller R. Enantioselective microbial reduction of substituted acetophenones. Tetrahedron: Asymmetry 2004, 15:1247-1258.
14. Lo H.H., Lin W.D., Hsu S.K., Hsu W.H. Asymmetrically simultaneous synthesis of l-homophenylalanine and N-6-protected-2-oxo-6-amino-hexanoic acid by engineered Escherichia coli aspartate aminotransferase. Biotechnol. Prog. 2009, 25:1637-1642.
15. Hwang J.Y., Park J., Seo J.H., Cha M., Cho B.K., Kim J., Kim B.G. Simultaneous synthesis of 2-phenylethanol and l-homophenylalanine using aromatic transaminase with yeast Ehrlich pathway. Biotechnol. Bioeng. 2009, 102:1323-1329.
16. Bradshaw C.W., Wong C.H., Hummel W., Kula M.R. Enzyme-catalyzed asymmetric-synthesis of (S)-2-amino-4-phenylbutanoic acid and (R)-2-hydroxy-4-phenylbutanoic acid. Bioorg. Chem. 1991, 19:29-39.
17. Busca P., Paradisi F., Moynihan E., Maguire A.R., Engel P.C. Enantioselective synthesis of non-natural amino acids using phenylalanine dehydrogenases modified by site-directed mutagenesis. Org. Biomol. Chem. 2004, 2:2684-2691.
18. Bommarius A.S., Schwarm M., Drauz K. Biocatalysis to amino acid-based chiral pharmaceuticals - examples and perspectives. J. Mol. Catal. B: Enzym. 1998, 5:1-11.
19. Asano Y., Yamada A., Kato Y., Yamaguchi K., Hibino Y., Hirai K., Kondo K. Enantioselective synthesis of (S)-amino acids by phenylalanine dehydrogenase from Bacillus sphaericus: use of natural and recombinant enzymes. J. Org. Chem. 1990, 55:5567-5571.
20. Kragl U., Kruse W., Hummel W., Wandrey C. Enzyme engineering aspects of biocatalysis: cofactor regeneration as example. Biotechnol. Bioeng. 1996, 52:309-319.
21. M. Politino, M.M. Cadin, P.M. Skonezny, J.G. Chen, Process for Preparing Dipeptidyl IV Inhibitors and Intermediates Therefor, The Patent Cooperation Treaty (PCT). U.S. Patent, WO 2005/106011 A3, 2005.
22. R. Hanson, M.J. Donovan, S. Goldberg, P.A. Jass, W.S. Li, R. Patel, K. Ramig, L.J. Szarka, J.J. Venit, Stereoselective Reductive Amination of Ketones, U.S. Patent 6,140,088, 2000.
23. Shaked Z., Whitesides G.M. Enzyme-catalyzed organic-synthesis - NADH regeneration by using formate dehydrogenase. J. Am. Chem. Soc. 1980, 102:7104-7105.
24. S.T. Chen, M.J. Tseng, T. Kao, B. Sookkheo, T. Surat, Facile Synthesis of l-Homophenylalanine By Equilibrium Shift Enzymatic Reaction Using Engineered Tyrosine Aminotransferase, U.S. Patent 6,146,859, 2000.