Efficient preparation of L-cysteic acid and its esters

L-beta-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-beta-haloalanines were prepared predominantly from L-serine via functional group transformation. Here we reported an alternative approach for the preparation of L-beta-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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Facile syntheses of l-β-haloalanine derivatives from l-cysteine or l-cystine

Tao

Luo

Huang

et al. 2008

Amino Acids

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Expeditious synthesis of 1-substituted taurines with diverse functionalized side-chains

Kakaei

Chen

2013

Tetrahedron

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Efficient preparation of L-cysteic acid and its esters

Abstract: Summary. L-Cysteic acid and its esters were prepared in good yields from the oxidation of L-cystine by chlorine in water and in alcohols. When the reaction was carried out in alcohols the corresponding esters were produced.

Cited by 2 publications

References 7 publications

Facile syntheses of l-β-haloalanine derivatives from l-cysteine or l-cystine

Facile syntheses of l-β-haloalanine derivatives from l-cysteine or l-cystine

Expeditious synthesis of 1-substituted taurines with diverse functionalized side-chains

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