Fluorinated carbohydrates as chemical probes for molecular recognition studies. Current status and perspectives

Abstract

<p>Fluorinated carbohydrates have become indispensable in glycosciences. This contribution provides an overview of how fluorine introduction modifies physical and chemical properties of carbohydrates along with selected examples of its applications.</p>

The Role of Fluorine in Glycomimetic Drug Design

“…A recent review by Linclau, et al., provides an excellent overview of the influence of fluorination on carbohydrate structure and conformation, as well as intra‐ and intermolecular F interactions [20] . It also describes the nomenclature of fluorinated glycomimetics, which is not covered here.…”

Introducing affinity and selectivity into galectin-targeting nanoparticles with fluorinated glycan ligands

“…24 Fluorination of glycans inuences their physicochemical properties and hence modulates their biological function. [25][26][27][28] While uorine substitution has little effect on glycan conformation, 29,30 it can inuence hydrogen bonding properties of adjacent hydroxyl groups, 31,32 and uorine itself is a weak hydrogen bond acceptor but not a hydrogen bond donor. 33,34 Furthermore, uorine atoms can form attractive multipolar interactions with proteins, 35,36 and these have been observed with uorinated carbohydrate derivatives, 37 including galectin binders.…”

Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

“…Therefore, the use of bioisosteres of carbohydrates functional groups is a popular approach in glycobiology [2]. As such, the synthesis of fluorosugars, including polyfluorinated analogues, is an interesting strategy to study biological systems [3][4][5][6][7]. The replacement of OH groups by fluorine atoms arise from their similarities in term of polarity and isosteric relationship [3,8].…”

“…For a long time, fluorinated carbohydrates have been used as a method to stabilize glycosidic bonds [9][10][11] or for epitope mapping [12,13]. More recently, heavily fluorinated carbohydrates were involved, among other things [5], in binding with UDP-Gal mutase [14], immunoglobulin [15,16], and glycogen phosphorylase [17].…”