Fluorous-based carbohydrate

Ko KS, Jaipuri FA, Pohl NL. Fluorous-based carbohydrate microarrays. J. Am. Chem. Soc. 2005 127 13162-13163. 

Direct Formation of Fluorous-based Carbohydrate Microrrays... 

In 2008, Pohl et al. [12f] described an innovative technology based on fluorous-based carbohydrate microarrays applied to demonstrate that both diastereomers of glycero-D-mannoheptoses fotmd in bacteria bind to ConA. These results showed that this plant lectin can accept modifications at the C-6 position of its natural mannose ligand. 

Figure 8.1 Fluorous-based carbohydrate microarrays allow the patterning of fluorous-tagged carbohydrates based on noncovalent fluorous—fluorous interactions.

Automated Solution-Phase Oligosaccharide Synthesis and Carbohydrate Microarrays Development of Fluorous-Based Tools for Glycomics... 

This group was used to protect carbohydrates for fluorous based synthesis. The ester is prepared using DCC (CH2CI2, DMAP, 87% yield) as a coupling agent. It is cleaved by methanolysis with NaOMe (2 h, rt, 93% yield). A similarly functionalized benzoyl ester has been prepared and tested as a protective group in fluorous... 

Noncovalent fluorous-based interactions have also been used to construct chemical arrays. The original concept of fluorous-based chemical arrays was demonstrated by Ko et al. with unprotected carbohydrate ligands [67]. Flu-orous tags are originally developed to simplify purification steps during the synthesis of small molecules [68], but they demonstrated the strength of the... 

A related strategy was used for synthesis of a more complex carbohydrate, the trisaccharide moiety of globotriaosyl ceramide (Gb3) [10b] (Scheme 3.19). In this reaction an acyl-based fluorous protecting group was used to facilitate the intermediate purification steps in a similar way as can be achieved by solid phase carbohydrate chemistry [12]. 

As fluorous Cbz-type hnkers are known to be partially deprotected in acidic medium, a base-labile amine-protecting group (19, Scheme 8.4) was developed as an orthogonal alternative. The peptide products were purified by both fluorous HPLC and FSPE [41]. The deprotection of the fluorous tag was carried out using 2% aqueous ammonia, a reagent that would raise concerns in the presence of common carbohydrate-protecting groups such as acetates. 

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