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Coupling and Decoupling of Diverse Molecular Units in Glycosciences pp 1–36Cite as

Synthesis of N-Linked Glycopeptides Using Convergent Enzymatic Glycosylation Combined with SPPS

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Abstract

Glycosylation of peptides and proteins has emerged as a promising strategy to improve the pharmacokinetic profile of peptide- and protein-based therapeutics. The synthesis of pure homogeneous N-linked glycopeptides and glycoproteins is a challenging task, and efficient routes to access them are in high demand. Endo-β-N-acetylglucosaminidise catalysed glycosylation of N-acetylglucosamine-tagged peptides, using activated oligosaccharide oxazolines as donors, has recently attracted attention due to the relative simplicity by which the process convergently affords glycoconjugates with complete control of stereo- and regioselectivity. Herein, a brief review of some examples of recent enzyme-mediated N-glycosylation used to synthesise glycopeptides with therapetic potential is provided.

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Authors and Affiliations

  1. School of Chemical Sciences, The University of Auckland, 23 Symonds St, Auckland, New Zealand

    Renata Kowalczyk, Harveen Kaur & Margaret A. Brimble

  2. Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland, 1010, New Zealand

    Antony J. Fairbanks & Margaret A. Brimble

  3. Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, 8140, New Zealand

    Antony J. Fairbanks

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  1. Renata Kowalczyk
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  1. Pharmaceutical Sciences Department, Wilkes University, Wilkes-Barre, Pennsylvania, USA

    Zbigniew J. Witczak

  2. Pharmaceutical Sciences Department, Nesbitt School of Pharmacy, Wilkes University, Wilkes-Barre, Pennsylvania, USA

    Roman Bielski

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Kowalczyk, R., Kaur, H., Fairbanks, A.J., Brimble, M.A. (2018). Synthesis of N-Linked Glycopeptides Using Convergent Enzymatic Glycosylation Combined with SPPS. In: Witczak, Z., Bielski, R. (eds) Coupling and Decoupling of Diverse Molecular Units in Glycosciences. Springer, Cham. https://doi.org/10.1007/978-3-319-65587-1_1

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