A site-specific method for deuteration: reduction of aryl halides with sodium borodeuteride and palladium chloride

Enzymatic synthesis of tryptamine and its halogen derivatives selectively labeled with hydrogen isotopes

“…The compound 8 , i.e., [4- 2 H]-tryptamine, labeled with deuterium in the 4-position of indole ring was synthesized by decarboxylation of [4′- 2 H]- l -Trp which was obtained by 1 H/ 2 H isotope exchange according the procedure described earlier [ 24 , 25 ]. The exchange was catalyzed with UV light produced by a 250 W mercury lamp.…”

“…[5- 2 H]-tryptamine was obtained by decarboxylation of [5′- 2 H]- l -Trp synthesized according earlier described procedures [ 18 , 25 ]. This intermediate [5′- 2 H]- l -Trp was obtained in two step synthesis: first 5-bromoindole was reduced by sodium borodeuteride, NaB 2 H 4 , to[5- 2 H]-indole [ 25 ], which in next step, catalyzed by enzyme tryptophanase ( l -tryptophan indole-lyase EC 4.1.99.1 ), was coupled with S -methyl- l -cysteine giving [5′- 2 H]- l -Trp [ 18 ] (Near 100 % deuterium incorporation in the 5′-position by 1 H NMR spectrum). The enzymatic decarboxylations of [4′- 2 H]-, and [5′- 2 H]- l -Trp, leading to 8 and 9 were carried out in 50 mM Tris–HCl buffer, pH 5.5.…”

Synthesis of four tritium‐labelled aminowarfarin methyl ketal regioisomers

“…Method G is based on a report of specific deuterium incorporation into aryl halides using NaBDd and Pd/C in CH30D (18). Use of this procedure on compounds B, 16, and 19…”

Regioselective deuterium labelling of aromatic acids, amides and amines using group VIII metal catalysts

“…The selective ortho-deuteration of these classes of compounds, or of simple derivatives, is conventionally performed either from specific synthetic precursors (1,2,3) or via directed ortho-lithiation reactions.…”