Synthesis of Mixed α/β2,2-Peptides by Site-Selective Ring-Opening of Cyclic Quaternary Sulfamidates

  1. Mazo, N. 1
  2. García-González, I. 1
  3. Navo, C.D. 1
  4. Corzana, F. 1
  5. Jiménez-Osés, G. 1
  6. Avenoza, A. 1
  7. Busto, J.H. 1
  8. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Organic Letters

ISSN: 1523-7060

Año de publicación: 2015

Volumen: 17

Número: 23

Páginas: 5804-5807

Tipo: Artículo

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DOI: 10.1021/ACS.ORGLETT.5B02927 SCOPUS: 2-s2.0-84948798274 WoS: WOS:000366152000021 GOOGLE SCHOLAR

Otras publicaciones en: Organic Letters

Objetivos de desarrollo sostenible

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2015/00062/001

Resumen

A method for site- and stereoselective peptide modification using a cyclic sulfamidate scaffold containing peptides is described. A peptide synthesis strategy allowing the rapid generation of mixed α/β-peptides incorporating a sulfamidate residue, derived from 2-methylisoserine, has been generalized. The unique electrophilic nature of this scaffold for nucleophilic substitution at a quaternary center with total inversion of its configuration, which was demonstrated computationally, allows for site-selective conjugation with various nucleophiles, such as anomeric thiocarbohydrates and pyridines. This strategy provides rapid access to complex thioglyco-α/β-conjugates and charged α/β-peptides. © 2015 American Chemical Society