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Glycopeptides

Glycopeptides, especially the glycan chains, have played pivotal roles in various biological activities and involved in numerous biological recognition events, such as immune system, endocrine system, protein folding and cell communication. Due to the natural linkage between glycan and the amino acid residues of peptide, glycopeptides can be classified into two principal types: N-linked and O-linked glycopeptides.

 

N-linked glycopeptides

  • N-linked glycosylated peptides are the most frequently found glycopeptides
  • They contain an amide bond between a glycan and the side chain of Asp, the so-called N-glycosidic bond
  • The sites of N-glycosylation in N-glycoproteins are characterized by sequons
  • Asn-Xaa-Ser/Thr (NXS/T, where Xaa is any amino acid except proline).
  • The carbohydrate moiety is more variable, including alpha- and beta-Glc and beta-N-acetylgalactosamine (GalNAc)

O-linked glycopeptides

  • O-linked glycoproteins are far more diversified than N-glycoproteins
  • Most abundant is the mucin-type with an alpha-linkage between GalNAc and serine or threonine
  • Examples of other saccharides linked to serine and threonine include alpha-galactose (Gal), glucose (Glc), fucose (Fuc), mannose (Man) and Xylose (Xyl)
  • A separate class of O-linked glycosylation, which appears to be functionally distinct, is the O-GlcNAc modification found as monosaccharides attached to either Ser or Thr

 

Glycoslyation of peptides has been an effective synthetic strategy to improve metabolic stability and enhance drug delivery. Glyco-amino acids used in solid phase peptide synthesis are Fmoc protected with the sugar generally protected as the fully acetylated form.

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References

  1. Rudd PM, et al. (2001) Glycosylation and the immune system. Science. 291(5512):2370-2376.
  2. Carganico S, et al. (2009) Building blocks for the synthesis of post-translationally modified glycated peptides and proteins. J. Pep. Sci. 15(2):67-71.
  3. Yamamoto T, et al. (2009) Improving metabolic stability by glycosylation: bifunctional peptide derivatives that are opioid receptor agonists and neurokinin 1 receptor antagonists. J. Med.Chem. 52(16):5164-5175.
  4. Moradi SV, et al. (2016) Glycosylation, an effective synthetic strategy to improve the bioavailability of therapeutic peptides. Chem. Sci. 7(4):2492-2500.

A selection of glycosylated amino acids that have been successfully incorporated into glycopeptides at InnoPep is shown below.

Please contact us for your specific request.

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About InnoPep

InnoPep Inc. is a company started by a couple of researchers with decades of expertise in peptide synthesis and conjugation aimed at enabling.

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