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  • Title: CD exciton chirality method for determination of the absolute configuration of beta-hydroxy-alpha-amino acid derivatives.
    Author: Lo LC, Chen JY, Yang CT, Gu DS.
    Journal: Chirality; 2001 May 15; 13(5):266-71. PubMed ID: 11317348.
    Abstract:
    The absolute configuration of beta-hydroxy-alpha-amino acids was studied by CD exciton chirality method using 7-diethylaminocoumarin-3-carboxylate as a red-shifted chromophore. The CD spectra of bischromophoric derivatives of (S)-serine and (2S,3R)-threonine methyl esters (2 and 7) were compared with those of acyclic vic-aminoalcohols and diols (3--6 and 8--9). This study indicates that the polar carboxylate group of beta-hydroxy-alpha-amino acids makes them a unique subclass of vic-aminoalcohols. By combining the data of CD and NMR coupling constants, we are able to correlate their preferred conformer B and positive CD to the corresponding absolute configuration.
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