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The labelling patterns in retrorsine (1) derived biosynthetically from [1,4-2H4]- and [2,3,-2H4]-putrescine have been established by 2H n.m.r. spectroscopy; in the former case the formation of (9S)-[9-2H]retrorsine (12) is consistent with stereospecific addition of hydrogen to the re-face of an aldehyde precursor (RC2HO).
J. Rana and D. J. Robins, J. Chem. Soc., Chem. Commun., 1983, 1222 DOI: 10.1039/C39830001222
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