Solid-Phase Library Synthesis of Carbohydrates

Solid-phase approaches may ease the product isolation and purification in the generation of larger oligosaccharide libraries. However, solid-support oligosaccharide synthesis requires thorough 

---

Taylor, C. M. The sulfoxide glycosylation method and its application to solid-phase oligosaccharide synthesis and the generation of combinatorial libraries. Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries 2001,41 -65. 

Kahne, Still and coworkers reported recently the solid-phase parallel synthesis and screening of a carbohydrate library using the sulfoxide glycosylation reaction. The library was constructed on TentaGel resin and contained approximately 1300 di- and trisaccharides. A chemical tag was incorporated after every reaction step in order to monitor the history of the beads and to facilitate structure elucidation. The synthesis of the library is outlined in Scheme 2.6.3. 

Other known oligonucleotide analogs include oligomers in which the heterocyclic bases have been modified [155] or replaced by other types of compound [156], Solid-phase syntheses of hybrids of DNA with peptides [157-163], with carbohydrates [164,165], and with PNA (peptide nucleic acids, see Section 16.4.1.2 [166-168]) have also been reported, and several strategies have been developed that enable the preparation of oligonucleotides with a modified 5 - or 3 -terminus [169-174] or of cyclic oligonucleotides [122,175], Various techniques for the parallel solid-phase synthesis of oligonucleotides have been developed for the preparation of compound libraries [176-181],... 

Automated carbohydrate synthesis allows for the production of complex carbohydrates orders of magnitude faster than other approaches. This advance has the potential to parallel the breakthroughs achieved by researchers in the peptide and DNA fields that opened up the pro-teomic and genomic eras in biotechnology. By increasing the scope of the carbohydrate building block library and streamlining the reaction conditions further we anticipate that automated solid-phase carbohydrate synthesis will become the method of choice for carbohydrate production. 

---