Expanding the conformational landscape of minimalistic tripeptides by their O-glycosylation

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Brito, Alexandra and Dave, Dhwanit and Lampel, Ayala and Castro, Vânia I. B. and Kroiss, Daniela and Reis, Rui L. and Tuttle, Tell and Ulijn, Rein V. and Pires, Ricardo A. and Pashkuleva, Iva (2021) Expanding the conformational landscape of minimalistic tripeptides by their O-glycosylation. Journal of the American Chemical Society, 143 (47). pp. 19703-19710. ISSN 1520-5126 (https://doi.org/10.1021/jacs.1c07592)

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Abstract

We report on the supramolecular self-assembly of tripeptides and their O-glycosylated analogues, in which the carbohydrate moiety is coupled to a central serine or threonine flanked by phenylalanine residues. The substitution of serine with threonine introduces differential side-chain interactions, which results in the formation of aggregates with different morphology. O-glycosylation decreases the aggregation propensity because of rebalancing of the π interactions. The glycopeptides form aggregates with reduced stiffness but increased thermal stability. Our results demonstrate that the designed minimalistic glycopeptides retain critical functional features of glycoproteins and therefore are promising tools for elucidation of molecular mechanisms involved in the glycoprotein interactome. They can also serve as an inspiration for the design of functional glycopeptide-based biomaterials.

  • Item type:Article
    ID code:78753
    Dates:
    Date
    Event
    1 December 2021
    Published
    19 November 2021
    Published Online
    1 November 2021
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:01 Dec 2021 16:26
    Last modified:21 Nov 2024 03:38
    URI:https://strathprints.strath.ac.uk/id/eprint/78753
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