Incubation of (2S,3S)-5-guanidino[2,3-2H2]-2-(2′-oxoazetidin-1′-yl)pentanoic acid and (2S,3R)-5-guanidino-[3-2H1]-2-(2′-oxoazetidin-1′-yl)pentanoic acid with clavaminic acid synthase resulted in highly stereospecific hydroxylation at C-3, with removal of the pro-R hydrogen or deuterium, respectively.
J. E. Baldwin, K. D. Merritt, C. J. Schofield, S. W. Elson and K. H. Baggaley, J. Chem. Soc., Chem. Commun., 1993, 1301 DOI: 10.1039/C39930001301
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