Abstract
l-β-Haloalanines are physiologically active unnatural amino acids and they are useful intermediates for the synthesis of natural and unnatural amino acids, S-linked glycopeptides, and lanthionines. In general l-β-haloalanines were prepared predominantly from l-serine via functional group transformation. Here we reported an alternative approach for the preparation of l-β-haloalanines via halogenation of protected l-cysteine esters which was obtained from l-cysteine or l-cystine, respectively. The mercapto group of protected l-cysteine esters was efficiently transformed to halo groups by triphenylphosphine/N-halosuccinimides. It has been proved to be a versatile desulfurization strategy via this functional group transformation.
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Financial support from the “Western Light” of the Chinese Academy of Sciences is gratefully acknowledged.
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Tao, F., Luo, Y., Huang, Q. et al. Facile syntheses of l-β-haloalanine derivatives from l-cysteine or l-cystine. Amino Acids 37, 603–607 (2009). https://doi.org/10.1007/s00726-008-0179-6
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DOI: https://doi.org/10.1007/s00726-008-0179-6