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Hydrogen transfer pathways of the asymmetric reduction of alpha,beta-unsaturated ketone mediated by baker's yeast.

Abstract：

:The hydrogen transfer mechanism of cofactor reduction and recycling processes in the yeast reduction of alpha,beta-unsaturated ketone was studied by using quantitative isotope tracing close to natural abundance measured by (2)H NMR. In the reaction, the active cofactor is NADPH. The cofactor-transferred hydride attacks the beta sp(2) carbon of the enone carbonyl while water hydrogen is transferred to the alpha position. The reductant involved in the reaction depends on the quantity of yeast. When the amount of yeast is very large, the enzymes use preferentially certain unidentified substance stored in the yeast cells rather than the added glucose as electron donor. In this case, the hydrogen transferred by the cofactor is mainly of water origin. When the yeast amount is low, the added glucose is more efficiently used by the enzymes as electron donor and its hydrogen atoms bound to C-1 and C-3 are delivered to the substrate.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Chu Y,Zhang BL,Silvestre V,Cheng JP

doi

10.1016/j.bioorg.2006.04.002

subject

Has Abstract

pub_date

2006-06-01 00:00:00

pages

158-66

issue

3

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(06)00026-5

journal_volume

34

pub_type

杂志文章

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