Diverse oligosaccharide syntheses

Lipoteichoic acid (LTA), which is a characteristic and widespread cell-surface constituent of gram-positive bacteria, is an amphiphile consisting of two covalently-bound distinct parts, i. e., a glycolipid and a hydrophilic poly(glycerol phosphate). 

---

In the synthesis of diverse oligosaccharide libraries, a conventional SPOS methodology would involve laborious solution-phase preparation of many building blocks and that number would increase if increased diversity of the library is to be obtained. To develop a versatile and practical approach, it is necessary to reduce the number of building blocks ideally... 

Sect. 2 below summarizes some of the important structures containing pyruvic acid acetals. The structural diversity, methods for structure elucidation, biosynthesis and biological function of these oligo- and polysaccharides will be briefly discussed. Sect. 3 gives an overview of the synthetic methods for the stereoselective preparation of pyruvated building blocks for oligosaccharide synthesis. Here, special attention is paid to pyruvated glycosyl donors, and their application to the synthesis of selected structures is presented in Sect. 4. 

Many of the methods used to illustrate the diverse reaction conditions employed for glycosidase mediated oligosaccharide synthesis have little or incomplete characterisation. Yields are calculated in a range of ways from the limiting reagent... 

A linker originally designed for solid-phase synthesis of peptides is the backbone amide linker (11) (BAL), this anchoring approach has now been extended to the combinatorial synthesis of diverse amide [31], hydroxamate [32], oligosaccharide [33] and heterocyclic small molecule libraries [34-36]. 

---