Recent trends in biomimetic NADH regeneration

Topics in Catalysis

Volumn 57, Issue 5, 2014, Pages 321-331

  Quinto, Tommaso ^a   Köhler, Valentin ^a   Ward, Thomas R ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Biomimetic chemistry; Compartmentalization; Mutual inhibition; NADH regeneration; Pianostool complex; Transfer hydrogenation

Indexed keywords

BIOMIMETIC CHEMISTRY; COMPARTMENTALIZATION; MUTUAL INHIBITION; NADH REGENERATION; PIANOSTOOL COMPLEX; TRANSFER HYDROGENATIONS;

AMIDES; BIOMIMETICS; ORGANOMETALLICS;

CATALYST REGENERATION;

EID: 84896556750     PISSN: 10225528     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11244-013-0187-y     Document Type: Article

References (54)

1. Abril O, Whitesides GM (1982) Hybrid organometallic/enzymatic catalyst systems: regeneration of NADH using dihydrogen. J Am Chem Soc 104:1552-1554
2. Ruppert R, Herrmann S, Steckhan E (1987) Efficient indirect electrochemical in situ regeneration of NADH: electrochemically drive enzymatic reduction of pyruvate catalized by D-LDH. Tetrahedron Lett 28:6583-6586
3. Hollmann F, Arends IWCE, Buehler K (2010) Biocatalytic redox reactions for organic synthesis: nonconventional regeneration methods. ChemCatChem 2:762-782
4. Mcskimming A, Colbran SB (2013) The coordiantion chemistry of organo-hydride donors: new prospects for efficient multi-electron reduction. Chem Soc Rev 42:5439-5488
5. + regeneration. Appl Microbiol Biotechnol 93:2251-2264
6. Hollmann F, Hofstetter K, Schmid A et al (2006) Non-enzymatic regeneration of nicotinamide and flavin cofactors for monooxygenase catalysis. Trends Biotechnol 24:163-171
7. Kohlmann C, Wolfgang M, Lütz S (2008) Electroenzymatic synthesis. J Mol Catal B Enzym 51:57-72
8. Rodriguez C, Lavandera I, Gotor V (2012) Recent advances in cofactor regeneration system applied to biocatalyzed oxidative process. Curr Org Chem 16:2525-2541
9. Truppo MD (2012) Cofactor recycling for enzyme catalyzed processes. Compre Chirality 7:46-70
10. Holtmann D, Schrader J (2007) Approaches to recycling and substituing NAD(P)H as a CYP cofactor. In: Schmid RD, Urlacher VB (eds) Modern biooxidation. Enzymes, reactions and applications. Willey, Weinheim, pp 265-290
11. Lütz S (2007) Transition metal-catalyzed regeneration of nicotinamide cofactors. In: de Vries JG, Elsevier CJ (eds) The handbook of homogeneous hydrogenation. Wiley, Weinheim, pp 1471-1482
12. Weckbecker A, Gröger H, Hummel W (2009) Regeneration of nicotinamide coenzymes: principles and applications for the synthesis of chiral compounds. In: Scheper T, Belkin S, Doran PM, Endo I, Gu MB, Hu WS, Mattiasson B, Nielsen J, Stephanopoulos GN, Ulber R, Zeng A-P, Zhong J-J, Zhou W (eds) Advances in biochemical engineering/biotechnology. Springer, Heidelberg, pp 195-242
13. Shaked Z, Barber JJ, Whitesides GM (1981) A Combined electrochemical/ enzymatic method for in situ regeneration of NADH based on cathodic reduction of cyclic disulfides. J Org Chem 46:4100-4101
14. DiCosimo R, Wong C-H, Daniels Lacy et al (1981) Enzyme-catalyzed organic synthesis: electrochemical regeneration of NAD(P)H from NAD(P) using methyl viologen and flavoenzymes. J Org Chem 46:4622-4623
15. +) and related compounds. Electrochemical redox pattern and allied chemical behavior. J Am Chem Soc 97:5083-5092
16. Kiwi J (1981) Photochemical generation of reduced α-nicotinamide- adenine dinucleotide (induced by visible light). J Photochem 16:193-202
17. Land EJ, Swallow AJ (1969) One-electron reactions in biochemical systems as studied by pulse radiolysis II riboflavin. Biochemistry 8:2117-2125
18. Wienkamp R, Steckhan E (1983) Selective generation of NADH by visible light. Angew Chem Int Ed 22:497
19. Wienkamp R, Steckhan E (1982) Indirect electrochemical regeneration of nadh by a bipyridinerhodium(I) complex as electron transfer agent. Angew Chem Int Ed 21:782-783
20. Franke M, Steckhan E (1988) Tris(2,2′-bipyridil-5-sulfonic acid)rhodium(III), an improved redox catalyst for the light-induced and the electrochemically initiated enzymatic reduction of carbonyl compounds. Angew Chem Int Ed 27:265-267
21. + with formate catalysed by cationic rhodium complexes. J Chem Soc Chem Commun 1:1150-1151
22. Shaked Z, Whiteside GM (1980) Enzyme-catalyzed organic synthesis: NADH regeneration by using formate dehydrogenase. J Am Chem Soc 102:7104
23. + analogues by a trans-dimethylcobalt(III) complex. J Chem Soc Perkin Trans 2:41-45
24. + in enzymatic synthesis. J Chem Soc Chem Commun 94:1706-1707
25. Kim JA, Kim S, Lee J et al (2012) Photochemical production of NADH using cobaloxime catalysts and visible-light energy. Inorg Chem 51:8057-8063
26. Fukuzumi S, Kotani H, Prokop KA, Goldberg DP (2011) Electron- and hydride-transfer reactivity of an isolable manganese(V)-oxo complex. J Am Chem Soc 133:1859-1869
27. Fukuzumi S, Kotani H, Lee Y-M, Nam W (2008) Sequential electron-transfer and proton-transfer pathways in hydride-transfer reactions from dihydronicotinamide adenine dinucleotide analogues to non-heme oxoiron(IV) complexes and p-chloranil. Detection of radical cations of NADH analogues in acid-promo. J Am Chem Soc 130:15134-15142
28. + by UV-vis spectroscopy - a kinetic analysis. Spectrochimica Acta Part A 74:678-684
29. Ali I, Gill A, Omanovic S (2012) Direct electrochemical regeneration of the enzymatic cofactor 1,4-NADH employing nano-patterned glassy carbon/Pt and glassy carbon/Ni electrodes. Chem Eng J 188:173-180
30. Damian A, Maloo K, Omanovic S (2007) Direct electrochemical regeneration of NADH on Au, Cu and Pt-Au electrodes. Chem Biochem Eng Q 21:21-32
31. Kobayashi A, Takatori R, Kikuchi I et al (2001) Formation of novel 1:1 adducts accompanied by regioselective hydride transfer from transition-metal hydrido complexes to NAD(P) models. Organometallics 20:3361-3363
32. Kobayashi A, Konno H, Sakamoto K et al (2005) Transition metal complexes coordinated by an NAD(P)H model compound and their enhanced hydride-donating abilities in the presence of a base. Chem Eur J 11:4219-4226
33. +/NADH on the copper nanodoped mercury monolayer carbon fiber electrode. J Electroanal Chem 665:12-19
34. + accompanied by generation and consumption of hydrogen with a water-soluble iridium complex at ambient pressure and temperature. J Am Chem Soc 134:367-374
35. + Catalyzed by a [C,N] and a [C,C] cyclometalated organoiridium complex at room temperature in water. J Am Chem Soc 134:9417-9427
36. Betanzos-lara S, Liu Z, Habtemariam A et al (2012) Organometallic ruthenium and iridium transfer-hydrogenation catalysts using coenzyme NADH as a cofactor. Angew Chem Int Ed 51:3897-3900
37. Liu Z, Deeth RJ, Butler JS et al (2013) Reduction of quinones by NADH catalyzed by organoiridium complexes. Angew Chem Int Ed 52:4194-4197
38. +. Organometallics 31:5958-5967
39. Fu Y, Romero JM, Habtemariam A et al (2012) The contrasting chemical reactivity of potent isoelectronic iminopyridine and azopiridine osmium(II) arene anticancer complexes. Chem Sci 3:2485-2494
40. + by ruthenium(II) arene complexes under biologically relevant conditions. J Biol Inorg Chem 11:483-488
41. Maid H, Böhm P, Huber SM et al (2011) Iron catalysis for in situ regeneration of oxidized cofactors by activation and reduction of molecular oxygen: a synthetic metalloporphyrin as a biomimetic NAD(P)H oxidase. Angew Chem Int Ed 50:2397-2400
42. 2+-catalyzed reduction of nicotinamide and flavin cofactors: characterization and application to promote chemoenzymatic reduction reactions. Appl Organomet Chem 24:380-385
43. Vrtis JM, White AK, Metcalf WW et al (2001) Phosphite dehydrogenase: an unusual phosphoryl transfer reaction. J Am Chem Soc 123:2672-2673
44. De Torres M, Dimroth J, Arends IWCE et al (2012) Towards recyclable NAD(P)H regeneration catalysts. Molecules 17:9835-9841
45. Nam DH, Park CB (2012) Visible light-driven NADH regeneration sensitized by proflavine for biocatalysis. ChemBioChem 13:1278-1282
46. 2-supported quantum dots. Chem Comm 47:4643-4645
47. Lee SH, Lee HJ, Won K, Park CB (2012) Artificial electron carriers for photoenzymatic synthesis under visible light. Chem Eur J 18:5490-5495
48. Lee SH, Kwon Y-C, Kim D-M, Park CB (2013) Cytochrome P450-catalyzed O-dealkylation coupled with photochemical NADPH regeneration. Biotechnol Bioeng 110:383-390
49. + for selective organic synthesis. J Organomet Chem 689:4783-4790
50. Hildebrand F, Lütz S (2009) Stable electroenzymatic processes by catalyst separation. Chem Eur J 15:4998-5001
51. 2+ and enzymes - analysis and potential remedies. J Mol Catal B Enzyme 63:149-156
52. Wang ZJ, Clary KN, Bergman RG et al (2013) A supramolucular approach to combining enzymatic and transition metal catalysis. Nat Chem 5:100-103
53. Köhler V, Wilson YM, Dürrenberger M et al (2013) Synthetic cascades are enabled by combining biocatalysts with artificial metalloenzymes. Nat Chem 5:93-99
54. Ward TR (2011) Artificial metalloenzymes based on the biotin-avidin technology: enantioselective catalysis and beyond. Acc Chem Res 44:47-57