Oligomerization solid-phase synthesis

Linkletter, B. A. Bruice, T. C. Solid-Phase Synthesis of Oligomeric De-oxynucleic Guanidine (DNG) A Polycationic Analogue of DNA, Bioorg. Med. Chem.. Lett. 1998, 8, 1285-1290. 

The synthetic protocols used for the preparation of oligonucleotides on supports can also be used to prepare oligomers from diols other than nucleosides. Symmetric or unsymmetric diols, such as N-acylated 4-hydroxyprolinol [268] or cyclopentane-derived diols (carbocyclic deoxyribose analogs [269]), can be selectively mono-trity-lated and then converted into a phosphoramidite that is suitable for the solid-phase synthesis of oligophosphates. An illustrative synthesis of protected //-phosphonates from diols, as well as their conversion on CPG into oligomeric phosphoramidates, are outlined in Figure 16.28. 

Figure 16.31. Solid-phase synthesis of oligomeric phenylalkynes [276,277,279,280],...

The solid phase synthesis of oligomeric amides using polystyrene graft intermediates is described (1). Other examples of polymeric assisted syntheses of heterocycles are provided (2). 

The solid-phase synthesis of DNA oligomers has reached a high level of maturity and is extensively used for the synthesis of primers for polymerase chain reaction or the design of new genes (13). In contrast to the cellular process, the synthetic route forms the polymer in 3 -to-5 direction. The oligomerization is carried out on CPG using a base labile linker. Typically, the nucleobases are introduced as acyl-protected phosphoramidites,... 

Solid-Phase Synthesis of Pseudopeptides and Oligomeric Peptide Backbone Mimetics... 

Memfield first introduced the concept of solid-phase peptide synthesis nearly half a century ago, and since then the use of heterogeneous materials to facilitate synthesis has evolved and become widespread in many contexts. For example, the automated solid-phase synthesis of oligomeric biomolecules, such as polypeptides and polynucleotides, has become the standard methodology for the production of such compounds. 

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