S-Michael additions to chiral dehydroalanines as an entry to glycosylated cysteines and a sulfa-tn antigen mimic

  1. Aydillo, C. 1
  2. Compañón, I. 1
  3. Avenoza, A. 1
  4. Busto, J.H. 1
  5. Corzana, F. 1
  6. Peregrina, J.M. 1
  7. Zurbano, M.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Journal of the American Chemical Society

ISSN: 0002-7863

Ano de publicación: 2014

Volume: 136

Número: 2

Páxinas: 789-800

Tipo: Artigo

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DOI: 10.1021/JA411522F SCOPUS: 2-s2.0-84892712061 WoS: WOS:000330018600045 GOOGLE SCHOLAR

Outras publicacións en: Journal of the American Chemical Society

Obxectivos de Desenvolvemento Sustentable

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Diseño racional de glicopéptidos con aplicaciones en Química Biológica

2013/00007/001

Resumo

Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(β-d-glucopyranosyl)-d-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-l-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied. © 2013 American Chemical Society.