Photosensitized NAD(P)H regeneration systems. Application in the reduction of butan-2-one, pyruvic, and acetoacetic acids and in the reductive amination of pyruvic and oxoglutaric acid to amino acid.

Citation:

Mandler D, Willner I. Photosensitized NAD(P)H regeneration systems. Application in the reduction of butan-2-one, pyruvic, and acetoacetic acids and in the reductive amination of pyruvic and oxoglutaric acid to amino acid. J. Chem. Soc., Perkin Trans. 2Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999). 1986;(6) :805 - 11.

Date Published:

1986///

Abstract:

NADH and NADPH were formed by a photosensitized enzyme-catalyzed process. NADPH was formed in the presence of ferredoxin NADP-reductase with Ru(bpy)32+ (bpy = 2,2'-bipyridine) as photosensitizer, Me viologen as primary electron acceptor, and (NH4)3 EDTA or 2-mercaptoethanol. Zn(II) meso-tetramethylpyridiniumporphyrin was used as photosensitizer for the photoinduced prodn. of NADH with the same reaction components but with lipoamide dehydrogenase as the enzyme catalyst. The photoinduced NADH/NADPH regeneration systems were coupled to secondary enzyme-catalyzed processes, e.g. the redn. of butan-2-one to butan-2-ol, pyruvic acid to lactic acid, or acetoacetic acid to β-hydroxybytyric acid; coupling to the reductive amination of pyruvic acid to alanine and of α-oxoglutaric acid to glutamic acid was also possible. The products showed high optical purity and the enzymes and coenzymes showed high turnover nos. and stability. [on SciFinder(R)]

Notes:

CAPLUS AN 1986:586857(Journal)