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Thiyl Glycosylation of Olefinic Proteins: S-Linked Glycoconjugate Synthesis


  • This work was supported by the International AIDS Vaccine Initiative (IAVI). We thank Profs. J. Blanchard and M. G. Finn for kindly providing pET23a/Np276 and p75 M/Qβ plasmids, respectively, and Dr. J. Errey for helpful discussions.


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Tagged for thiolation: A novel glycoconjugation strategy utilizes a non-natural olefin-containing amino acid (homoallylglycine, Hag) as a “tag” for modification and a photoinitiated hydroglycothiolation reaction that is selective only for the Hag olefinic “tag”. Application of this method to a number of model proteins allowed complete and precise site-selective glycosylation generating glycoconjugates that include, for example, virus-like particles displaying up to 180 glycans at preselected positions (see scheme).