Abstract
This practitioner protocol describes the synthesis of a family of deuterated nicotinamide cofactors: [4S‐2H]NADH, [4R‐2H]NADH, [4‐2H2]NADH and [4‐2H]NAD+. The application of a recently developed H2‐driven heterogeneous biocatalyst enables the cofactors to be prepared with high (>90%) 2H‐incorporation with 2H2O as the only isotope source.
Highlights
Nicotinamide cofactors in their oxidised (NAD+) and reduced (NADH) forms (Figure 1) mediate electron transfer in a wide range of redox enzyme-catalysed reactions
We have recently reported a route to deuterated NADH that uses H2 as the reducing agent and 2H2O as the source of deuterium isotopes.[4]
We describe how, by extension of the heterogeneous biocatalytic method described above, [4R-2H]NADH, [4-2H2]NADH and [4-2H]NAD+ may all be prepared, in addition to [4S-2H]
Summary
Nicotinamide cofactors in their oxidised (NAD+) and reduced (NADH) forms (Figure 1) mediate electron transfer in a wide range of redox enzyme (oxidoreductase)-catalysed reactions. Deuterated and tritiated forms of NADH may be prepared by reducing NAD+ in 2H2O (D2O)/3H2O (T2O) with sodium dithionite,[2] or in 1H2O with a deuteride/tritide salt.[5] simple, these methods lack selectivity as to which face of the nicotinamide ring the 2H/3H atom is added.
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