DeoxyArbutin, (dA) a nanomolar, competitive inhibitor of mammalian tyrosinase <i>in vitro</i>, possesses excellent skin-lightening ability <i>in vivo</i>, probably through this mechanism although other mechanisms, such as via its anti-oxidant ability, have also been suggested. We recently developed a method for separating the enantiomers of deoxyArbutin, in part to further elucidate its mechanism of action, using novel chiral chromatography. We now report the determination of the absolute configuration of the single stereocenter (C1) of the molecule. To obtain this information we undertook a program of derivitization of one of the enantiomers, followed by creation of an x-ray quality single crystal for x-ray crystallographic analysis, which revealed the absolute configuration of that enantiomer of dA.

Determination of the absolute configuration of a single enantiomer of deoxyArbutin

249th National Meeting (2015)

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