Tn Antigen Mimics Based on sp2-Iminosugars with Affinity for an anti-MUC1 Antibody

  1. Fernández, E.M.S. 3
  2. Navo, C.D. 2
  3. Martínez-Sáez, N. 1
  4. Gonçalves-Pereira, R. 3
  5. Somovilla, V.J. 1
  6. Avenoza, A. 2
  7. Busto, J.H. 2
  8. Bernardes, G.J.L. 16
  9. Jiménez-Osés, G. 24
  10. Corzana, F. 2
  11. Fernández, J.M.G. 5
  12. Mellet, C.O. 3
  13. Peregrina, J.M. 2
  1. 1 University of Cambridge
    info

    University of Cambridge

    Cambridge, Reino Unido

    ROR https://ror.org/013meh722

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  3. 3 Universidad de Sevilla
    info

    Universidad de Sevilla

    Sevilla, España

    ROR https://ror.org/03yxnpp24

  4. 4 Universidad de Zaragoza
    info

    Universidad de Zaragoza

    Zaragoza, España

    ROR https://ror.org/012a91z28

  5. 5 Instituto de Investigaciones Químicas
    info

    Instituto de Investigaciones Químicas

    Sevilla, España

  6. 6 Universidade de Lisboa
    info

    Universidade de Lisboa

    Lisboa, Portugal

    ROR https://ror.org/01c27hj86

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Revista:
Organic Letters

ISSN: 1523-7060

Ano de publicación: 2016

Volume: 18

Número: 15

Páxinas: 3890-3893

Tipo: Artigo

DOI: 10.1021/ACS.ORGLETT.6B01899 SCOPUS: 2-s2.0-84981232791 WoS: WOS:000381236300096 GOOGLE SCHOLAR

Outras publicacións en: Organic Letters

Resumo

The first examples of amino acid (Ser/Thr)-sp2-iminosugar glycomimetic conjugates featuring an α-O-linked pseudoanomeric linkage are reported. The key synthetic step involves the completely diastereoselective α-glycosylation of Ser/Thr due to strong stereoelectronic and conformational bias imposed by the bicyclic sp2-iminosugar scaffold. Mucin-related glycopeptides incorporating these motifs were recognized by the monoclonal antibody (mAb) scFv-SM3, with activities depending on both the hydroxylation pattern (Glc/Gal/GlcNAc/GalNAc) of the sp2-iminosugar and the peptide aglycone structure (Ser/Thr). © 2016 American Chemical Society.