Alditol thiacrowns via a ring-closing metathesis of carbohydrate-derived α,ω-dithioallylethers

Benazza, Mohammed; Danquigny, Alain; Novogrocki, Guy; Valgimigli, Luca; Amorati, Riccardo; Ferroni, Fiammetta; Demailly-Mullie, Catherine; Siriwardena, Aloysius; Lesur, David; Aubry, Frédérick; Demailly, Gilles

doi:10.1016/j.tet.2015.06.049

Cited by 2 publications

(1 citation statement)

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“…Several methodologies have been developed for the preparation of thiosugars . Among the most recent examples, a general one‐pot synthesis of thiosugars 64 by double nucleophilic displacement from various alditol precursors 65 (with xylo‐, ribo‐, manno‐, gluco‐, galacto‐, and fuco‐configurations) was reported by Zhang et al (Figure A).…”

Section: Endocyclic Oxygen Replacementmentioning

confidence: 99%

Design and synthesis of glycomimetics: Recent advances

Tamburrini

Colombo

Bernardi

2019

Medicinal Research Reviews

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In the past few decades, our understanding of glycan information‐encoding power has notably increased, thus leading to a significant growth also in the design and synthesis of glycomimetic probes. Combining data from multiple analytical sources, such as crystallography, nuclear magnetic resonance spectroscopy, and other biophysical methods (eg, surface plasmon resonance and carbohydrate microarrays) has allowed to shed light on the key interaction events between carbohydrates and their protein‐targets. However, the low metabolic stability of carbohydrates and their high hydrophilicity, which translates in low bioavailability, undermine their development as drugs. In this framework, the design of chemically modified analogues (called carbohydrate mimics or glycomimetics) appears as a valid alternative for the development of therapeutic agents. Glycomimetics, as structural and functional mimics of carbohydrates, can replace the native ligands in the interaction with target proteins, but are designed to show enhanced enzymatic stability and bioavailability and, possibly, an improved affinity and selectivity toward the target. In the present account, we specifically focus on the most recent advances in the design and synthesis of glycomimetics. In particular, we highlight the efforts of the scientific community in the development of straightforward synthetic procedures for the preparation of sugar mimics and in their preliminary biological evaluation.

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Section: Endocyclic Oxygen Replacementmentioning

confidence: 99%