Syntheses of 1- and 6-S- and 1- and 6-Se-derivatives of 2-amino-2-deoxy-α/β-<scp>D</scp>-glucopyranose

Chen, George C.; Banks, Catherine H.; Irgolic, Kurt J.; Zingaro, Ralph A.

doi:10.1039/p19800002287

Cited by 10 publications

(1 citation statement)

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“…Thiol or selenol replacement of carbohydrate OH functional groups is not entirely common, likely given the difficulty in synthesis and isolation of these compounds caused by their propensity to dimerize into disulfides and diselenides. Examples of both dimers and alkylated thio-/selenoether derivatives have been presented in the literature and studied for various biological applications, such as their adjuvant/immunostimulatory abilities, carcinostatic activities, and antioxidant properties [123,124,125].…”

Section: Replacement Of Oh Functional Groupsmentioning

confidence: 99%

Bioisosteres of Carbohydrate Functional Groups in Glycomimetic Design

Hevey

2019

Biomimetics

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The aberrant presentation of carbohydrates has been linked to a number of diseases, such as cancer metastasis and immune dysregulation. These altered glycan structures represent a target for novel therapies by modulating their associated interactions with neighboring cells and molecules. Although these interactions are highly specific, native carbohydrates are characterized by very low affinities and inherently poor pharmacokinetic properties. Glycomimetic compounds, which mimic the structure and function of native glycans, have been successful in producing molecules with improved pharmacokinetic (PK) and pharmacodynamic (PD) features. Several strategies have been developed for glycomimetic design such as ligand pre-organization or reducing polar surface area. A related approach to developing glycomimetics relies on the bioisosteric replacement of carbohydrate functional groups. These changes can offer improvements to both binding affinity (e.g., reduced desolvation costs, enhanced metal chelation) and pharmacokinetic parameters (e.g., improved oral bioavailability). Several examples of bioisosteric modifications to carbohydrates have been reported; this review aims to consolidate them and presents different possibilities for enhancing core interactions in glycomimetics.

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Section: Replacement Of Oh Functional Groupsmentioning

confidence: 99%