Recent Advances in the Synthesis of Carbohydrate Mimetics

Abstract

Highly diverse strategies are employed to mimic carbohydrates. Two subgroups of carbohydrate mimetics are very important: alterations of the core structure and modifications of the O-glycosidic linkage. This review presents methods, most of them developed in the 21 st century, to mimic carbohydrates with a focus on their synthesis. A wide range of different reactions are discussed in order to access carbohydrate-like structures.

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

“…Since carbohydrates play a crucial role in biochemistry, compounds mimicking their structure and/or function (carbohydrate mimetics) have attracted great attention in academic research and in drug development [1–3]. These mimetics should not have the drawbacks of carbohydrates such as low binding affinity or instability [4–5].…”

Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides

“…More recently, Mong and co-workers synthesized fused glucopyranose oxazolines in nitrile solvents from thioglycoside donors and applied them to the synthesis of α(1→5)-arabinan [38]. Thus, the exploration of carbohydrate-based oxazolines [39–40] has been limited to serve as glycosyl donors or as intermediates for N -glycan synthesis. Although, a few pyranose-based oxazoline frameworks are known [41], the corresponding furanoid spiro [42] 2-oxazolines [43] are limited, to the best of our knowledge.…”

Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins

“…These include lectin-carbohydrate recognition 1,2,3 and processes catalyzed by glycosidases, 4,5,6 glycosyltransferases 7 and glycogen phosphorylases. 8 Very often modified carbohydrates are used to investigate these processes 9,10 and to create suitable inhibitors of the aforementioned enzymes. 1,2,3-Triazole modified carbohydrates became easily available after the discovery of the Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction and quickly became a prominent class of non-natural sugars.…”