Carbohydrate‐Based Molecular Scaffolding

Velter, Ingrid; Ferla, Barbara La; Nicotra, Francesco

doi:10.1080/07328300600733020

Cited by 52 publications

(3 citation statements)

References 154 publications

(65 reference statements)

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“…Following this breakthrough, carbohydrates made their way into combinatorial chemistry and have since been used as scaffolds for library generation [3–6] . Fused and spirocyclic systems, prepared by introducing a second or even a third ring onto the carbohydrate backbone, often enable improved carbohydrate‐receptor interactions [7,8] . Several groups have used an iodocyclization reaction to introduce a tetrahydrofuran motif to obtain such bi‐ and tricyclic carbohydrate scaffolds [9–14] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates

et al. 2023

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A reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether functionality serves as a handle that enables modification in biological systems via photoclick chemistry. The approach is based on the regioselec-tive oxidation of the C-3 hydroxy group in gluco-configured pyranosides, followed by stereoselective indium-mediated allylation. The ring formation is induced by an iodocyclization reaction with a neighboring hydroxy group. Subsequent dehydrohalogenation affords the desired methylene-tetrahydrofuran-containing carbohydrates.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates

et al. 2023

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“…Since Hirschmann et al first reported that the peptidomimetic based on β- d -glucoside scaffold ( Figure 5A ) could target somatostatin receptor, several research groups have reported the various applications of peptidomimetics based on carbohydrate scaffolds in different biological fields ( Hirschmann et al, 1992 ; Hirschmann et al, 2009 ). Relevant studies of peptidomimetics have been reviewed extensively elsewhere ( Cipolla et al, 2005 ; Meutermans et al, 2006 ; Velter et al, 2006 ; Cipolla et al, 2010 ; Tian et al, 2015 ; Lenci and Trabocchi, 2020 ). However, the existing examples have also demonstrated the difficulty of designing single carbohydrate scaffold mimetics that maintain the level of bioactivity (and/or selectivity) of the counterparts.…”

Section: Introductionmentioning

confidence: 99%

Exploring Carbohydrates for Therapeutics: A Review on Future Directions

Wang

Zhang

et al. 2021

Front. Pharmacol.

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Carbohydrates are important components of foods and essential biomolecules performing various biological functions in living systems. A variety of biological activities besides providing fuel have been explored and reported for carbohydrates. Some carbohydrates have been approved for the treatment of various diseases; however, carbohydrate-containing drugs represent only a small portion of all of the drugs on the market. This review summarizes several potential development directions of carbohydrate-containing therapeutics, with the hope of promoting the application of carbohydrates in drug development.

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“…Recently, the study of multivalency with glycosidases and other carbohydrate processing enzymes has been extended to polymeric scaffolds with pending carbohydrate motifs, emerging as an important tool for the study of such interactions. Thus, the anchor of a bioactive compound to a polymer backbone provides the possibility to target the polymer to a particular position in vivo, being this feature significant due to its potential applicability in materials science and biomedicine [32,33].…”

Section: Introductionmentioning

confidence: 99%