Review
Enzyme-catalysed biotransformations through photochemical regeneration of nicotinamide cofactors

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Abstract

Photosensitized regeneration of NAD(P)H cofactors by photochemical means is reviewed. Reductive regeneration of NAD(P)H cofactors proceeds through coupling of photogenerated N,N′dimethyl-4,4′-bipyridinium radical cation, which acts as electron carrier, to the enzymes lipoamide dehydrogenase, LipDH and ferredoxin reductase, FDR, respectively. Regeneration of NAD(P)H is also accomplished by substitution of the enzymes and electron carrier by synthetic rhodium complexes acting as H-donors for the regeneration of NAD(P)H. Various photosensitizers such as Ru(II)-tris-bipyridine, Ru(bpy)2+3, or Zn-meso-tetramethyl-pyridinium porphyrin, Zn-TMPyP4+, are applied in the systems. The photoinduced processes are initiated through oxidative or reductive electron-transfer quenching pathways. The photoregenerated NAD(P)H cofactors are coupled to subsequent biotransformations in such reduction of ketones and keto-acid, synthesis of amino-acids, and CO2-fixation processes. Oxidative regeneration of NAD(P)+ cofactors is accomplished by photochemical means. In these systems, Sn(II)-meso-tetramethylpyridinium porphyrin, Sn-TMPyP4+, Ru(bpy)2+3or acridine dyes are used as photosensitizers. Oxidation of NAD(P)H proceeds either by reductive quenching of the excited photosensitizer by NAD(P)H or dark oxidation of NAD(P)H by the oxidized photoproduct formed in the photosensitized electron-transfer process. The systems are applied in the dehydrogenation of alcohols, hydroxy acids, and amino acids.

References (110)

  • G. Nagy et al.

    Anal. Chim. Acta

    (1973)
  • J. Campbell et al.

    Biochim. Biophys. Acta

    (1975)
  • K. Dalziel
  • J.A. Olson et al.

    J. Biol. Chem.

    (1953)
  • W. Tischer et al.

    Biochemie

    (1980)
  • S.S. Godbole et al.

    Enzyme Microb. Technol.

    (1983)
  • G.L. Lemiere et al.

    Tetrahedron Lett.

    (1985)
  • M. Aizawa et al.

    Biochim. Biophys. Acta

    (1975)
  • H. Jaegfeldt et al.

    Anal. Chem.

    (1981)
  • O. Warburg et al.

    Biochemische Z.

    (1935)
  • V. Balzani et al.

    Pure Appl. Chem.

    (1979)
  • H.B. Gray et al.

    Science

    (1981)
  • T. Matsuo et al.

    Coord. Chem. Rev.

    (1980)
  • M.-P. Pileni et al.

    J. Phys. Chem.

    (1980)
  • P. Cuendet et al.

    Photochem. Photobiol.

    (1984)
  • A.F. Wagner et al.
  • F.A. Robinson
  • J.N. Lowe et al.
  • C. Walsh

    Acc. Chem. Res.

    (1980)
  • B.M. Guirard et al.

    Comprehen. Biochem.

    (1964)
  • L.J. Reed

    Comprehen. Biochem.

    (1967)
  • J. Moss et al.

    Adv. Enzymol.

    (1971)
  • R.W. Hay
  • M.B. Cohen et al.

    J. Nucl. Med.

    (1974)
  • J.R. Barrio et al.

    J. Med. Chem.

    (1982)
  • C. Walsh
  • D.W. Hutchinson
  • R.M. Bock
  • D. Grans et al.

    J. Org. Chem.

    (1983)
  • B.L. Hirschbein et al.

    J. Org. Chem.

    (1982)
  • K. Burton et al.

    Biochem. J.

    (1953)
  • H.K. Chenault et al.

    Appl. Biochem. Biotech.

    (1987)
  • G.M. Whitesides et al.

    Aldrichimca Acta

    (1983)
  • H. Dugas et al.
  • Z. Shaked et al.

    J. Amer. Chem. Soc.

    (1980)
  • R. Wichman et al.

    Biotech. Bioeng.

    (1981)
  • C.-H. Wong et al.

    J. Amer. Chem. Soc.

    (1985)
  • C.-H. Wong et al.

    J. Amer. Chem. Soc.

    (1981)
  • B.L. Hirschbein et al.

    J. Amer. Chem. Soc.

    (1982)
  • S.S. Wang et al.

    Adv. Biochem. Eng.

    (1979)
  • A.M. Klibanov et al.

    Biotech. Lett.

    (1980)
  • P. Ergerer et al.

    Biotech. Lett.

    (1982)
  • B. Danielson et al.

    Biotech. Lett.

    (1982)
  • B. Payen et al.

    Biotech. Lett.

    (1983)
  • Y. Miura et al.

    Agric. Biol. Chem.

    (1981)
  • I. Krube et al.

    Biotech. Bioeng.

    (1980)
  • L.G. Lee et al.

    J. Amer. Chem. Soc.

    (1985)
  • L.G. Lee et al.

    J. Org. Chem.

    (1986)
  • C.-H. Wong et al.

    J. Org. Chem.

    (1982)
  • G. Carrea et al.

    Biotech. Bioorg.

    (1986)
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