Strategies for regeneration of nicotinamide coenzymes emphasizing self-sufficient closed-loop recycling systems

Journal of Biotechnology

Volumn 191, Issue , 2014, Pages 22-31

  Hummel, Werner ^a   Gröger, Harald ^b  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b BIELEFELD UNIVERSITY   (Germany)

Author keywords

Closed loop; Coenzyme regeneration; Dehydrogenases; Oxidoreductases; Self sufficient

Indexed keywords

ACETONE; AMIDES; COENZYMES; GLUCOSE; RECYCLING;

CLOSED-LOOP; COENZYME REGENERATION; DEHYDROGENASES; OXIDO-REDUCTASES; SELF-SUFFICIENT;

REDOX REACTIONS;

2 PROPANOL; ACETONE; ALCOHOL DEHYDROGENASE; AMINO ACID; FORMATE DEHYDROGENASE; FORMIC ACID; GLUCOSE; GLUCOSE DEHYDROGENASE; HYDROXYACID; HYDROXYL GROUP; NICOTINAMIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; URSODEOXYCHOLIC ACID; COENZYME; NICOTINAMIDE ADENINE DINUCLEOTIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; COENZYME; ENZYME MECHANISM; EPIMERIZATION; METABOLISM; OXIDATION REDUCTION REACTION; REGENERATION; BIOCATALYSIS; BIOSYNTHESIS; CHEMISTRY;

2-PROPANOL; ALCOHOL DEHYDROGENASE; BIOCATALYSIS; COENZYMES; FORMATE DEHYDROGENASES; GLUCOSE 1-DEHYDROGENASE; NAD; NADP; NIACINAMIDE; OXIDATION-REDUCTION;

EID: 84911887971     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2014.07.449     Document Type: Article

References (47)

1. Abalain J.H., Di Stefano S., Amet Y., Quemener E., Abalain-Colloc M.L., Floch H.H. Cloning, DNA sequencing and expression of (3-17)beta hydroxysteroid dehydrogenase from Pseudomonas testosteroni. J. Steroid Biochem. Mol. Biol. 1993, 44:133-139.
2. Bakonyi D., Wirtz A., Hummel W. Large-scale enzymatic synthesis of 12-ketoursodeoxycholic acid from dehydrocholic acid by simultaneous combination of 3α-hydroxysteroid dehydrogenase from Pseudomonas testosteroni and 7β-hydroxysteroid dehydrogenase from Collinsella aerofaciens. Z. Naturforsch. 2012, 67b:1037-1044.
3. Boonstra B., Rathbone D.A., Bruce N.C. Engineering novel biocatalytic routes for production of semisynthetic opiate drugs. Biomol. Eng. 2001, 18:41-47.
4. Bossow B., Wandrey C. Continuous enzymatically catalyzed production of l-leucine from the corresponding racemic hydroxy acid. Ann. N. Y. Acad. Sci. 1987, 506:325-336.
5. Chen Y., Chen C., Wu X. Dicarbonyl reduction by single enzyme for the preparation of chiral diols. Chem. Soc. Rev. 2012, 41:1742-1753.
6. Constantinou A., Ghiotto F., Lam K.F., Gavriilidis A. Stripping of acetone from water with microfabricated and membrane gas-liquid contactors. Analyst 2014, 139:266-272.
7. Crosignani A., Setchell K.D.R., Invernizzi P., Larghi A., Rodrigues C.M.P., Podda M. Clinical pharmacokinetis of therapeutic bile acids. Clin. Pharmacokinet. 1996, 30:333-358.
8. 3 building block in organic synthesis. Angew. Chem. Int. Ed. 2005, 44:1304-1325.
9. Gargiulo S., Opperman D.J., Hanefeld U., Arends I.W.C.E., Hollmann F. A biocatalytic redox isomerisation. Chem. Commun. 2012, 48:6630-6632.
10. Gröger H., Borchert S., Kraußer M., Hummel W. Enzyme-catalyzed asymmetric reduction of ketones. Enzyme catalysis in Organic Synthesis 2012, 1037-1110. Wiley-VCH, Weinheim. 3rd ed. K. Drauz, H. Gröger, O. May (Eds.).
11. Gröger H., Hummel W., Metzner R. Reduction: asymmetric biocatalytic reduction of ketones. Comprehensive Chirality 2012, 181-215. Elsevier, Amsterdam. E.M. Carreira, H. Yamamoto (Eds.).
12. +-reducing [NiFe]-hydrogenase by a combination of immobilisation and chemical modification. J. Mol. Catal. B: Enzym. 2013, 97:169-174.
13. Hirano S., Masuda N., Oda H., Imamura T. Transformation of bile acids by mixed microbial cultures from human feces and bile acid transforming activities of isolated bacteria strains. Microbiol. Immunol. 1981, 25:271-282.
14. Hummel W., Gröger H. Enzyme-catalyzed reductive amination. Enzyme catalysis in Organic Synthesis 2012, 1165-1203. Wiley-VCH, Weinheim. 3rd ed. K. Drauz, H. Gröger, O. May (Eds.).
15. Itoh N., Matsuda M., Mabuchi M., Dairi T., Wang J. Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH. Eur. J. Biochem. 2002, 269:2394-2402.
16. Johannes T.W., Woodyer R.D., Zhao H.M. Efficient regeneration of NADPH using an engineered phosphite dehydrogenase. Biotechnol. Bioeng. 2007, 96:18-26.
17. Kara S., Schrittwieser J.H., Hollmann F. Strategies for cofactor regeneration in biocatalyzed reductions. Synthetic methods for biologically active molecules 2014, 209-238. Wiley-VCH, Weinheim. E. Brenna (Ed.).
18. Keinan E., Seth K.K., Lamed R. Synthetic applications of alcohol-dehydrogenase from Thermoanaerobium brockii. Ann. N. Y. Acad. Sci. 1987, 501:130-149.
19. Kizaki N., Yasohara Y., Hasegawa J., Wada M., Kataoka M., Shimizu S. Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes. Appl. Microbiol. Biotechnol. 2001, 55:590-595.
20. Levy S.B. Dihydroxyacetone-containing sunless or self-tanning lotions. J. Am. Acad. Dermatol. 1992, 27:989-993.
21. Macdonald I.A., Rochon Y.P., Hutchison D.M., Holdeman L.V. Formation of ursodeoxycholic acid from chenodeoxycholic acid by a 7β-hydroxysteroid dehydrogenase-elaborating Eubacterium aerofaciens strain cocultured with 7α-hydroxysteroid dehydrogenase-elaborating organisms. Appl. Environ. Microbiol. 1982, 44:1187-1195.
22. Makino Y., Inoue K., Dairi T., Itoh N. Engineering of phenylacetaldehyde reductase for efficient substrate conversion in concentrated 2-propanol. Appl. Environ. Microbiol. 2005, 71:4713-4720.
23. Makino Y., Itoh N. Development of an improved phenylacetaldehyde reductase mutant by an efficient selection procedure. Appl. Microbiol. Biotechnol. 2013, 98:4437-4443.
24. Mallin H., Wulf H., Bornscheuer U.T. A self-sufficient Baeyer-Villiger biocatalysis system for the synthesis of e{open}-caprolactone from cyclohexanol. Enzyme Microb. Technol. 2013, 53:283-287.
25. Mansson M.-O., Larsson P.-O., Mosbach K. Covalent binding of an NAD analogue to liver alcohol dehydrogenase resulting in an enzyme-coenzyme complex not requiring exogenous coenzyme for activity. Eur. J. Biochem. 1978, 86:455-463.
26. Matsuda T., Yamanaka R., Nakamura K. Recent progress in biocatalysis for asymmetric oxidation and reduction. Tetrahedron: Asymmetry 2009, 20:513-557.
27. Müller C.A., Akkapurathu B., Winkler T., Staudt S., Hummel W., Gröger H., Schwaneberg U. In vitro double-oxidation of n-heptane with direct co-factor regeneration. Adv. Synth. Catal. 2013, 355:1787-1798.
28. Müller M., Wolberg M., Schubert T., Hummel W. Enzyme-catalyzed regio- and enantioselective ketone reductions. Adv. Biochem. Eng. Biotechnol. 2005, 92:261-287.
29. Pedrini P., Andreotti E., Guerrini A., Dean M., Fantin G., Giovannini P.P. Xanthomonas maltophilia CBS 897.97 as a source of new 7β- and 7α-hydroxysteroid dehydrogenases and cholylglycine hydrolase: improved biotransformations of bile acids. Steroids 2006, 71:189-198.
30. Salen G., Colalillo A., Verga D., Bagan E., Tint G.S., Shefer S. Effect of high and low-doses of ursodeoxycholic acid on gallstone dissolution in humans. Gastroenterology 1980, 78:1412-1418.
31. Schmidt E., Vasic-Racki D., Wandrey C. Enzymatic production of l-phenylalanine from the racemic mixture of d,l-phenyllactate. Appl. Microbiol. Biotechnol. 1987, 26:42-48.
32. Setlhaku M., Heitmann S., Gorak A., Wichmann R. Investigation of gas stripping and pervaporation for improved feasibility of two-stage butanol production process. Bioresour. Technol. 2013, 136:102-108.
33. Shaked Z., Whitesides G.M. Enzyme-catalyzed organic synthesis: NADH regeneration by using formate dehydrogenase. J. Am. Chem. Soc. 1980, 102:7104-7105.
34. Staudt S., Burda E., Giese C., Müller C.A., Marienhagen J., Schwaneberg U., Hummel W., Drauz K., Gröger H. Direct oxidation of cycloalkanes to cycloalkanones with oxygen in water. Angew. Chem. Int. Ed. 2013, 52:2359-2363.
35. Stillger T., Bönitz M., Villela Filho M., Liese A. Überwindung von thermodynamischen Limitierungen in substratgekoppelten Cofaktorregenerierungsverfahren. Chem. Ing. Tech. 2002, 74:1035-1039.
36. Sutherland J.D., Macdonald I.A. The metabolism of primary, 7-oxo- and 7b-hydroxy bile acids by Clostridium absonum. J. Lipid Res. 1982, 23:726-732.
37. Thoden J.B., Hegeman A.D., Wesenberg G., Chapeau M.C., Frey P.A., Holden H.M. Structural analysis of UDP-sugar binding to UDP-galactose 4-epimerase from Escherichia coli. Biochemistry 1997, 36:6294-6304.
38. Thoden J.B., Holden H.M. Dramatic differences in binding of UDP-galactose and UDP-glucose to UDP-galactose 4-epimerase from Escherichia coli. Biochemistry 1998, 37:11469-11477.
39. Wandrey C., Fiolitakis E., Wichmann R., Kula M.-R. l-Amino acids from a racemic mixture of α-hydroxy acids. Ann. N. Y. Acad. Sci. 1984, 434:91-94.
40. Weckbecker A., Gröger H., Hummel W. Regeneration of nicotinamide coenzymes: principles and applications for the synthesis of chiral compounds. Adv. Biochem. Eng. Biotechnol. 2010, 120:195-242.
41. Willetts A.J., Knowles C.J., Levitt M.S., Roberts S.M., Sandey H., Shipston N.F. Biotransformation of endo-bicyclo[2.2.1]heptan-2-ols and endo-bicyclo[3.2.0]hept-2-en-6-ol into the corresponding lactones. J. Chem. Soc., Perkin Trans. 1991, 1:1608-1610.
42. Winkelhausen E., Kuzmanova S. Microbial conversion of d-xylose to xylitol. J. Ferment. Bioeng. 1998, 86:1-14.
43. Winkler C.K., Tasnádi G., Clay D., Hall M., Faber K. Asymmetric bioreduction of activated alkenes to industrially relevant optically active compounds. J. Biotechnol. 2012, 162:381-389.
44. Winkler T., Hummel W., Gröger H. Enantioselective rearrangement coupled with water addition: direct synthesis of enantiomerically pure saturated carboxylic acids from α, β-unsaturated aldehydes. ChemCatChem 2014, 6:961-964.
45. Wohlgemuth R. Development of sustainable biocatalytic reduction processes. Synthetic Methods for Biologically Active Molecules 2014, 1-25. Wiley-VCH, Weinheim. E. Brenna (Ed.).
46. Wulf H., Mallin H., Bornscheuer U.T. Protein engineering of a thermostable polyol dehydrogenase. Enzyme Microb. Technol. 2012, 51:217-224.
47. Zhang Y., Gao F., Zhang S.-P., Su Z.-G., Ma G.-H., Wang P. Simultaneous production of 1,3-dihydroxyacetone and xylitol from glycerol and xylose using a nanoparticle-supported multi-enzyme system with in situ cofactor regeneration. Bioresour. Technol. 2011, 102:1837-1843.