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Labilization of the 3 carbon hydrogens in chelated 2s aspartic acid and erythro 2s 3 methyl aspartic acid and threo 2s 3 methyl aspartic acid



Labilization of the 3 carbon hydrogens in chelated 2s aspartic acid and erythro 2s 3 methyl aspartic acid and threo 2s 3 methyl aspartic acid



Journal of the American Chemical Society 98(14): 4150-4154



Aspartic acid chelated to Co(III) as a tridentate ligand in s-cis-aspartato(triamine) Co(III) will selectively deuterate with retention of configuration to give 3-deuterioaspartic acid as established by proton NMR spectroscopy. The deuterated amino acid was characterized after removal from the complex. The position of deuteration was confirmed by the preparation and deuteration of the erythro and threo isomers of s-cis-(2S)-3-methylaspartato(diethylenetriamine) Co(III). The deuterium exchange studies revealed that the labile proton is the erythro proton. Alkyl protons adjacent only to a ligated carboxylate can be labilized and supports previous studies which suggest that ring flexibility is an important factor in determining lability.

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