Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition

  1. Gutiérrez-Jiménez, M.I. 2
  2. Aydillo, C. 1
  3. Navo, C.D. 2
  4. Avenoza, A. 2
  5. Corzana, F. 2
  6. Jiménez-Osés, G. 23
  7. Zurbano, M.M. 2
  8. Busto, J.H. 2
  9. Peregrina, J.M. 2
  1. 1 University of Copenhagen
    info

    University of Copenhagen

    Copenhague, Dinamarca

    ROR https://ror.org/035b05819

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  3. 3 Universidad de Zaragoza
    info

    Universidad de Zaragoza

    Zaragoza, España

    ROR https://ror.org/012a91z28

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Revue:
Organic Letters

ISSN: 1523-7060

Année de publication: 2016

Volumen: 18

Número: 12

Pages: 2796-2799

Type: Article

DOI: 10.1021/ACS.ORGLETT.6B00840 SCOPUS: 2-s2.0-84975317301 WoS: WOS:000378303400002 GOOGLE SCHOLAR

D'autres publications dans: Organic Letters

Résumé

A second generation of chiral bicyclic dehydroalanines easily accessible from serine has been developed. These scaffolds behaved as excellent S-Michael acceptors when tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-galactopyranose (abbreviated as GalNAc-α-SH) was used as a nucleophile. This addition proceeds with total chemo- and stereoselectivity, complete atom economy, quickly, and at room temperature, making it a true click reaction. The Michael adducts were easily transformed into S-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-l- and -d-cysteines, which can be regarded as mimics of the Tn antigen derived from l-Ser (α-d-GalNAc-l-Ser) and d-Ser (α-d-GalNAc-d-Ser), respectively. © 2016 American Chemical Society.