Towards preparative asymmetric synthesis of β-hydroxy-α-amino acids: l-allo-Threonine formation from glycine and acetaldehyde using recombinant GlyA

Journal of Biotechnology

Volumn 130, Issue 4, 2007, Pages 402-410

  Makart, Stefan ^a   Bechtold, Matthias ^a   Panke, Sven ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Aldolase; C C bond formation; Diastereomers; Enzyme kinetics; Enzyme membrane reactor

Indexed keywords

C-C BOND FORMATION; DIASTEREOMERS; ENZYME MEMBRANE REACTORS; ENZYME STABILITY;

ALDEHYDES; BIOSYNTHESIS; ENZYME KINETICS; PH EFFECTS; STEREOSELECTIVITY;

AMINO ACIDS;

ACETALDEHYDE; AMINO ACID; BETA HYDROXY ALPHA AMINO ACID DERIVATIVE; GLY A ENZYME; GLYCINE; LEVO ALLO THREONINE; RECOMBINANT ENZYME; THREONINE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME MEMBRANE BIOREACTOR; ENZYME STRUCTURE; ESCHERICHIA COLI; NONHUMAN; PRIORITY JOURNAL;

ENZYME ACTIVATION; ENZYME STABILITY; GLYCINE; GLYCINE HYDROXYMETHYLTRANSFERASE; RECOMBINANT PROTEINS; STEREOISOMERISM; THREONINE;

ESCHERICHIA COLI;

EID: 34347374271     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2007.05.008     Document Type: Article

References (41)

1. Batra R., and Gupta M.N. Enhancement of enzyme activity in aqueous-organic solvent mixtures. Biotechnol. Lett. 16 (1994) 1059-1064
2. Bechtold M., Makart S., Heinemann M., and Panke S. Integrated operation of continuous chromatography and biotransformations for the generic high yield production of fine chemicals. J. Biotechnol. 124 (2006) 146-162
3. Bradford M.M. Rapid and sensitive method for quantitation of microgram quantities of protein utilizing principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
4. Breuer M., and Hauer B. Carbon-carbon coupling in biotransformation. Curr. Opin. Biotechnol. 14 (2003) 570-576
5. Castro G.R., and Knubovets T. Homogeneous biocatalysis in organic solvents and water-organic mixtures. Crit. Rev. Biotechnol. 23 (2003) 195-231
6. DeSantis G., Liu J.J., Clark D.P., Heine A., Wilson I.A., and Wong C.H. Structure-based mutagenesis approaches toward expanding the substrate specificity of d-2-deoxyribose-5-phosphate aldolase. Bioorg. Med. Chem. 11 (2003) 43-52
7. Edelkraut F., and Brockmann U. Simultaneous determination of carboxylic acids and carbonyl compounds in estuaries by HPLC. Chromatographia 30 (1990) 432-435
8. Einarsson S., Josefsson B., and Lagerkvist S. Determination of amino acids with 9-fluorenylmethyl chloroformate and reversed-phase high-performance liquid chromatography. J. Chromatogr. 282 (1983) 609-618
9. Espelt L., Bujons J., Parella T., Calveras J., Joglar J., Delgado A., and Clapes P. Aldol additions of dihydroxyacetone phosphate to N-Cbz-amino aldehydes catalyzed by l-fuculose-1-phosphate aldolase in emulsion systems: inversion of stereoselectivity as a function of the acceptor aldehyde. Chem. Eur. J. 11 (2005) 1392-1401
10. Espelt L., Parella T., Bujons J., Solans C., Joglar J., Delgado A., and Clapes P. Stereoselective aldol additions catalyzed by dihydroxyacetone phosphate-dependent aldolases in emulsion systems: preparation and structural characterization of linear and cyclic iminopolyols from aminoaldehydes. Chem. Eur. J. 9 (2003) 4887-4899
11. Fernandez M.M., Clark D.S., and Blanch H.W. Papain kinetics in the presence of a water-miscible organic solvent. Biotechnol. Bioeng. 37 (1991) 967-972
12. Fessner W.-D. In: Patel R.N. (Ed). Enzymatic Asymmetric Synthesis using Aldolases (2000), Stereoselective Biocatalysis 239-265
13. Gijsen H.J.M., and Wong C.H. Unprecedented asymmetric aldol reactions with 3 aldehyde substrates catalyzed by 2-deoxyribose-5-phosphate aldolase. J. Am. Chem. Soc. 116 (1994) 8422-8423
14. Goldberg R.N., and Tewari Y.B. Thermodynamics of enzyme-catalyzed reactions. Part 4. Lyases. J. Phys. Chem. Ref. Data 24 (1995) 1669-1698
15. Goldberg R.N., Tewari Y.B., and Bhat T.N. Thermodynamics of enzyme-catalyzed reactions-a database for quantitative biochemistry. Bioinformatics 20 (2004) 2874-2877
16. Greenberg W.A., Varvak A., Hanson S.R., Wong K., Huang H.J., Chen P., and Burk M.J. Development of an efficient, scalable, aldolase-catalyzed process for enantioselective synthesis of statin intermediates. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5788-5793
17. Jackson B.G., Pedersen S.W., Fisher J.W., Misner J.W., Gardner J.P., Staszak M.A., Doecke C., Rizzo J., Aikins J., Farkas E., et al. Enantioselective syntheses of 1-carbacephalosporins from chemoenzymically derived β-hydroxy-α-amino acids: applications to the total synthesis of carbacephem antibiotic Loracarbef. Tetrahedron 56 (2000) 5667-5677
18. Khmelnitsky Y.L., Mozhaev V.V., Belova A.B., Sergeeva M.V., and Martinek K. Denaturation capacity: a new quantitative criterion for selection of organic solvents as reaction media in biocatalysis. Eur. J. Biochem. 198 (1991) 31-41
19. Kim M.J., Hennen W.J., Sweers H.M., and Wong C.H. Enzymes in carbohydrate synthesis: N-acetylneuraminic acid aldolase catalyzed reactions and preparation of N-acetyl-2-deoxy-d-neuraminic acid derivatives. J. Am. Chem. Soc. 110 (1988) 6481-6486
20. Kimura T., Vassilev V.P., Shen G.-J., and Wong C.-H. Enzymatic synthesis of β-hydroxy-α-amino acids based on recombinant d- and l-threonine aldolases. J. Am. Chem. Soc. 119 (1997) 11734-11742
21. Kragl U., Gygax D., Ghisalba O., and Wandrey C. Enzymatic two-step synthesis of N-acetylneuraminic acid in the enzyme membrane reactor. Angew. Chem. Int. Ed. Engl. 30 (1991) 827-828
22. Kragl U., Kruse W., Hummel W., and Wandrey C. Enzyme engineering aspects of biocatalysis: cofactor regeneration as example. Biotechnol. Bioeng. 52 (1996) 309-319
23. Kragl U., Niedermeyer U., Kula M.R., and Wandrey C. Engineering aspects of enzyme engineering-continuous asymmetric C-C bond formation in an enzyme-membrane-reactor. Ann. NY Acad. Sci. 613 (1990) 167-175
24. Liese A., Karutz M., Kamphuis J., Wandrey C., and Kragl U. Enzymatic resolution of 1-phenyl-1,2-ethanediol by enantioselective oxidation: Overcoming product inhibition by continuous extraction. Biotechnol. Bioeng. 51 (1996) 544-550
25. Liese A., Seelbach K., and Wandrey C. Industrial Biotransformation (2006), Wiley-VCH, Weinheim
26. Liu J.Q., Odani M., Yasuoka T., Dairi T., Itoh N., Kataoka M., Shimizu S., and Yamada H. Gene cloning and overproduction of low-specificity d-threonine aldolase from Alcaligenes xylosoxidans and its application for production of a key intermediate for parkinsonism drug. Appl. Microbiol. Biotechnol. 54 (2000) 44-51
27. Lozano P., deDiego T., and Iborra J.L. Influence of water-miscible aprotic solvents on α-chymotrypsin stability. Biotechnol. Prog. 12 (1996) 488-493
28. Lye G.J., and Woodley J.M. Application of in situ product-removal techniques to biocatalytic processes. Trends Biotechnol. 17 (1999) 395-402
29. Mahmoudian M., Noble D., Drake C.S., Middleton R.F., Montgomery D.S., Piercey J.E., Ramlakhan D., Todd M., and Dawson M.J. An efficient process for production of N-acetylneuraminic acid using N-acetylneuraminic acid aldolase. Enzyme Microb. Technol. 20 (1997) 393-400
30. alkB-expression system as an efficient tool for the production of recombinant proteins in Escherichia coli fed-batch fermentations. Biotechnol. Bioeng. 96 (2007) 326-336
31. Marquardt W. Model-based experimental analysis of kinetic phenomena in multi-phase reactive systems. Chem. Eng. Res. Des. 83 (2005) 561-573
32. Panke S., and Wubbolts M. Advances in biocatalytic synthesis of pharmaceutical intermediates. Curr. Opin. Chem. Biol. 9 (2005) 188-194
33. Roels J.A. Energetics and Kinetics in Biotechnology (1983), Elsevier Biomedical Press
34. Saeed A., and Young D.W. Synthesis of l-β-hydroxyaminoacids using serine hydroxymethyltransferase. Tetrahedron 48 (1992) 2507-2514
35. Salagnad C., Godde A., Ernst B., and Kragl U. Enzymatic large-scale production of 2-keto-3-deoxy-d-glycero-d-galacto-nonopyranulosonic acid in enzyme membrane reactors. Biotechnol. Prog. 13 (1997) 810-813
36. Samland A.K., and Sprenger G.A. Microbial aldolases as C-C bonding enzymes-unknown treasures and new developments. Appl. Microbiol. Biotechnol. 71 (2006) 253-264
37. Schirch L. Serine hydroxymethyltransferase. Adv. Enzymol. Relat. Areas Mol. Biol. 53 (1982) 83-112
38. Schirch V., Hopkins S., Villar E., and Angelaccio S. Serine hydroxymethyltransferase from Escherichia coli: purification and properties. J. Bacteriol. 163 (1985) 1-7
39. Silvestri M.G., Desantis G., Mitchell M., and Wong C.H. Asymmetric aldol reactions using aldolases. Top. Stereochem. 23 (2003) 267-342
40. Straathof A.J.J. Development of a computer program for analysis of enzyme kinetics by progress curve fitting. J. Mol. Catal. B: Enzym. 11 (2001) 991-998
41. Wichmann R., Wandrey C., Buckmann A.F., and Kula M.R. Continuous enzymatic transformation in an enzyme membrane reactor with simultaneous NAD(H) regeneration. Biotechnol. Bioeng. 23 (1981) 2789-2802