Six chiral deuterium labelled metabolic probes, ( R) and ( S)-enantiomers of [1,10,10- 2H 3]-hexadecan-1-ol, (11 E)-[1,10,10- 2H 3]-hexadec-11-en-1-ol and (11 Z)-[1,10,10- 2H 3]-hexadec-11-en-1-ol, were synthesized to examine the stereospecificity of the fatty alcohol oxidase from the female pheromone gland of the tobacco hawk moth ( Manduca sexta, Sphingidae). Both in vitro and in vivo oxidations were found to proceed by selective removal of the C1–H R hydrogen or deuterium atom ( Re-specificity) to yield the corresponding aldehydes. ( R) and ( S)-enantiomers of deuterium labelled salicyl alcohol and 2-thienyl-methanol, compounds entirely chemically diverse from the natural pheromone precursors, were also oxidised Re-specifically to salicylaldehyde and 2-thiophenecarb-aldehyde, respectively.