Trimethylamine W-oxide

Metabolism of trimethylamine oxide in fish muscle involves an enzyme-catalyzed oxidation-reduction reaction. The enzyme responsible for the conversion of trimethylamine oxide to trimethylamine is known as trimethylamine-W-oxide reductase. This enzyme acts on nicotinamide adenine dinucleotide (NADH) and TMAO to produce NAD+, trimethylamine and water (Fig. 13.13.1). TMAO acts as the oxidizing agent and is reduced, while NADH undergoes oxidation as the reducing agent. 

Oxidation of 3-borahomoadamantane adduct 77 with trimethylamine W-oxide leads to cis,cis-triol 110 (Scheme 43) <2003JA12179>. 

The conversion of (+)-8 to R-lf was accomplished through the intermediate fl-allyl species 9R (Scheme 4).,h The lf->3 conversion was carried out as is oudined in Scheme 1 to give 3R which produces the (IOR, 2 S) isomer R-lg in >98% de and (-)-(2/ )-butanol in >96% ee after trimethylamine W-oxide (TMANO) oxidation. Preliminary results have also been obtained for 2,3-dihydrofuran (84% de), c -2-butene (>85% defrom 95 5 c/t mixture),... 

As has been observed previously for Os3(CO)9(/ 3-77 77 t) -C6H6), the coordination mode of the [2.2]-paracyclo-phane ligand in Ru3(CO)9(jU3- 7 77 77 -Ci6Hi6) can be adjusted to a terminal mode by reaction with diphenyl-acetylene in the presence of trimethylamine-A -oxide the alkyne caps the triruthenium face in the place of the arene. When the reaction is conducted thermally in the absence of trimethylamine-W-oxide, additional products are also observed, including a related compound formed by insertion of a CO ligand into the alkyne-metal bond as shown in Scheme 3. 

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See also in sourсe #XX -- [ ]

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