2. Academic Validation
  3. Photoinduced addition of glycosyl thiols to alkynyl peptides: use of free-radical thiol-yne coupling for post-translational double-glycosylation of peptides

Photoinduced addition of glycosyl thiols to alkynyl peptides: use of free-radical thiol-yne coupling for post-translational double-glycosylation of peptides

  • J Org Chem. 2010 Jul 2;75(13):4644-7. doi: 10.1021/jo1008178.
Mauro Lo Conte 1,  Salvatore Pacifico,  Angela Chambery,  Alberto Marra,  Alessandro Dondoni
Affiliations

Affiliation

  • 1 Dipartmento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy.
PMID: 20527977 DOI: 10.1021/jo1008178
Abstract

Double glycosylation of cysteine-containing Peptides has been carried out by a one-pot two-step sequence comprising selective S-propargylation followed by photoinduced (lambda (max) 365 nm) free-radical hydrothiolation with glycosyl thiols. Conditions were established for the sequential introduction of two different thiol residues such as a glycosyl and a biotinyl derivative.

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