Chemoselective solution- and solid-phase synthesis of disulfide-linked glycopeptides
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2022-10Author
Banisalman, Katreen A.F.Polykandritou, A.
Mprah Barnieh, Francis

Morais, Goreti R.
Falconer, Robert A.
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© 2022 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0 .Peer-Reviewed
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openAccessAccepted for publication
2022
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Glycosylation of peptides and proteins is a widely employed strategy to mimic important post-translational modifications or to modulate the physicochemical properties of peptides to enhance their delivery. Furthermore, glycosylation via a sulfur atom imparts increased chemical and metabolic stability to the resulting glycoconjugates. Herein, we report a simple and chemoselective procedure to prepare disulfide-linked glycopeptides. Acetate-protected glycosylsulfenyl hydrazines are shown to be highly reactive with the thiol group of cysteine residues within peptides, both in solution and as part of conventional solid-phase peptide synthesis protocols. The efficiency of this glycosylation methodology with unprotected carbohydrates is also demonstrated, which avoids the need for deprotection steps and further extends its utility, with disulfide-linked glycopeptides produced in excellent yields. Given the importance of glycosylated peptides in structural glycobiology, pharmacology, and therapeutics, the methodology outlined provides easy access to disulfide-linked glycopeptides as molecules with multiple biological applications.Version
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Banisalman KA, Polykandritou A, Barnieh FM et al (2022) Chemoselective solution- and solid-phase synthesis of disulfide-linked glycopeptides. The Journal of Organic Chemistry. 87(21): 14026-14036.Link to Version of Record
https://doi.org/10.1021/acs.joc.2c01651Type
Articleae974a485f413a2113503eed53cd6c53
https://doi.org/10.1021/acs.joc.2c01651