Enantioselective reduction of carbonyl compounds by whole-cell biotransformation, combining a formate dehydrogenase and a (R)-specific alcohol dehydrogenase

Applied Microbiology and Biotechnology

Volumn 66, Issue 6, 2005, Pages 629-634

  Ernst, Marianne ^a   Kaup, Björn ^a   Müller, Michael ^a   Bringer Meyer, Stephanie ^a   Sahm, Hermann ^a  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ESCHERICHIA COLI; ESTERS; KETONES; OXIDATION;

ALCOHOL DEHYDROGENASE; CARBONYL COMPOUNDS; METHYL ACETOACETATE; WHOLE-CELL BIOTRANSFORMATION SYSTEMS;

CELL CULTURE;

ACETOACETIC ACID; ALCOHOL DEHYDROGENASE; CARBONYL DERIVATIVE; FORMATE DEHYDROGENASE; HYDROXYACID; KETONE DERIVATIVE; OXOACID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

BIOTRANSFORMATION; CARBONYL COMPOUND; MICROBIOLOGY;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CONTROLLED STUDY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ESCHERICHIA COLI; GENE EXPRESSION; LACTOBACILLUS BREVIS; MYCOBACTERIUM VACCAE; NONHUMAN; OXIDATION REDUCTION REACTION; PRODUCTIVITY; PROTEIN EXPRESSION; REDUCTION; WHOLE CELL;

ESCHERICHIA COLI; LACTOBACILLUS BREVIS; MYCOBACTERIUM VACCAE;

EID: 15244362096     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-004-1765-5     Document Type: Article

References (36)

1. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
2. Doig SD, Simpson H, Alphand V, Furstoss R, Woodley JM (2003) Characterization of a recombinant Escherichia coli TOP10 [pQR239] whole-cell biocatalyst for stereoselective Baeyer-Villiger oxidations. Enzyme Microb Technol 32:347-355
3. Endo T, Koizumi S (2001) Microbial conversion with cofactor regeneration using genetically engineered bacteria. Adv Synth Catal 343:521-526
4. Galkin A, Kulakova L, Tishkov V, Esaki N, Soda K (1995) Cloning of formate dehydrogenase gene from a methanol-utilizing bacterium Mycobacterium vaccae N10. Appl Microbiol Biotechnol 44:479-483
5. Galkin A, Kulakova L, Yoshimura T, Soda K, Esaki N (1997) Synthesis of optically active amino acids from alpha-keto acids with Escherichia coli cells expressing heterologous genes. Appl Environ Microbiol 63:4651-4656
6. +-specific formate dehydrogenase from Candida methylica allows the enzyme to use NADP. Biotechnol Lett 23:283-287
7. Haberland J, Hummel W, Dausmann T, Liese A (2002) New continuous production process for enantiopure (2R, 5R)-hexanediol. Org Proc Res Dev 6:458-462
8. Ham W-H, Oh C-Y, Lee Y-S, Jeong J-H (2000) A new synthesis of a key intermediate of β-lactam antibiotics via diastereoselective alkylation of β-hydroxy ester. J Org Chem 65:8372-8374
9. Hanahan D (1983) Studies on transformation of Escherichia coli with plasmids. J Mol Biol 166:557-580
10. Hummel W (1997) New alcohol dehydrogenases for the synthesis of chiral compounds. Adv Biochem Eng Biotechnol 58:145-184
11. Hummel W (1999) Large-scale applications of NAD(P)-dependent oxidoreductases: recent developments. Trends Biotechnol 17:487-491
12. + substrate. US patent 6,413,750 B1
13. Kataoka M, Yamamoto K, Kawabata H, Wada M, Kita K, Yanase H, Shimizu S (1999) Stereoselective reduction of ethyl 4-chloro-3-oxobutanoate by Escherichia coli transformant cells coexpressing the aldehyde reductase and glucose dehydrogenase genes. Appl Microbiol Biotechnol 51:486-490
14. Kataoka M, Kita K, Wada M, Yasohara Y, Hasegawa J, Shimizu S (2003) Novel bioreduction system for the production of chiral alcohols. Appl Microbiol Biotechnol 62:437-445
15. Kaup B, Bringer-Meyer S, Sahm H (2004) Metabolic engineering of Escherichia coli: construction of an efficient biocatalyst for D-mannitol formation in a whole-cell biotransformation. Appl Microbiol Biotechnol 64:333-339
16. Kihumbu D, Stillger T, Hummel W, Liese A (2002) Enzymatic synthesis of all stereoisomers of 1-phenylpropane-1,2-diol. Tetrahedron Asymm 13:1069-1072
17. Kovach EM, Elzer PH, Hill DS, Robertson GT, Farris MA, Roop RM II, Peterson KM (1995) Four new derivatives of the broad-host-range cloning vector pBBR1MCS, carrying different antibiotic-resistance cassettes. Gene 166:175-176
18. Miller JH (1972) Experiments in molecular genetics. Cold Spring Harbor Laboratory, Cold Spring Harbor, N.Y., pp 352-355
19. Niefind K, Müller J, Riebel B, Hummel W, Schomburg D (2003) The crystal structure of R-specific alcohol dehydrogenase from Lactobacillus brevis suggests the structural basis of metal dependency. J Mol Biol 327:317-328
20. Okuda K, Urabe I, Okada H (1985) Coenzymic activity of NADP derivatives alkylated at 2′-phosphate and 6-amino groups. Eur J Biochem 147:249-253
21. Rabinowitz MH, Andrews RC, Becherer JD, Bickett DM, Bubacz DG, Conway JG, Cowan DJ, Gaul M, Glennon K, Lambert MH, Leesnitzer MA, McDougald DL, Moss ML, Musso DL, Rizzolio MC (2001) Design of selective and soluble inhibitors of tumor necrosis factor-alpha converting enzyme (TACE). J Med Chem 44:4252-4267
22. Reichmuth DS, Kittle JL, Blanch HW, Keasling JD (2000) Biodesulfurization of dibenzothiophene in Escherichia coli is enhanced by expression of a Vibrio harveyi oxidoreductase gene. Biotechnol Bioeng 67:72-79
23. Riebel B (1996) Biochemische und molekularbiologische Charakterisierung neuer mikrobieller NAD(P)-abhängiger Alkohol-dehydrogenasen. PhD thesis, University of Düsseldorf, Düsseldorf
24. Sambrook J, Fritsch EF, Maniatis T (1989) Molecular cloning: a laboratory manual, 2nd edn. Cold Spring Harbor Laboratory, Cold Spring Harbor, N.Y.
25. Schoemaker HE, Mink D, Wubbolts MG (2003) Dispelling the myths - biocatalysis in industrial synthesis. Science 299:1694-1697
26. Schubert T, Hummel W, Kula MR, Müller M (2001) Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases. Eur J Org Chem 4181-4187
27. Schubert T, Hummel W, Müller M (2002) Highly enantioselective preparation of multifunctionalized propargylic building blocks. Angew Chem Int Edn 41:634-637
28. Schütte H, Flossdorf J, Sahm H, Kula M-R (1976) Purification and properties of formaldehyde dehydrogenase and formate dehydrogenase from Candida boidinii. Eur J Biochem 62:151-160
29. Serov AE, Popova AS, Fedorchuk VV, Tishkov V.I. (2002) Engineering of coenzyme specificity of formate dehydrogenase from Saccharomyces cerevisiae. Biochem J 367:841-847
30. Shaked Z, Whitesides GM (1980) Enzyme-catalyzed organic synthesis: NADH regeneration by using formate dehydrogenase. J Am Chem Soc 102:7105-7107
31. Tchieu JH, Norris V, Edwards JS, Saier MH Jr (2001) The complete phosphotransferase system in Escherichia coli. J Mol Microbiol Biotechnol 3:329-346
32. Tischer W, Tiemeyer W, Simon H (1980) Stereospecific hydrogenations with immobilized microbial cells or enzymes. Biochimie 62:331-339
33. +-specific formate dehydrogenases. Biotechnol Bioeng 64:187-193
34. Walton AZ, Stewart JD (2002) An efficient enzymatic Baeyer-Villiger oxidation by engineered Escherichia coli cells under non-growing conditions. Biotechnol Prog 18:262-268
35. Wolberg M, Hummel W, Wandrey C, Müller M (2000) Highly regio and enantioselective reduction of 3,5-dioxocarboxylates. Angew Chem Int Edn 39:4306-4308
36. Wolberg M, Hummel W, Müller M (2001) Biocatalytic reduction of β,δ-diketo esters: a highly stereoselective approach to all four stereoisomers of a chlorinated β,δ-dihydroxy hexanoate. Chem Eur J 7:4562-4571