SOLID-PHASE SYNTHESIS OF SEQUENCE-SPECIFIC PHENYLACETYLENE OLIGOMERS

SOLID-PHASE SYNTHESIS OF SEQUENCE-SPECIFIC PHENYLACETYLENE OLIGOMERS 

JEFFREY S. MOORE, DAVID J. HILL, and MATTHEW J. MIO The University of Illinois at Urbana-Champaign 

Solid-phase organic synthesis (SPOS) is an established technique for generation of peptides, nucleotides, and more recently, carbohydrates (oli-gosaccharides). - Supported syntheses of nonbiological oligomers and other small moleculeshave also been reported, reflecting the method s 

Solid-phase organic syntheses of nonbiological oligomers have advantages over solution-phase methods with respect to sequence control, ease of purification, and speed. The products can be well-defined oligomers that are unlike the mixtures usually obtained in classical polymer syntheses. This chapter explores some recent developments in this area, with an emphasis on our own work at the University of Illinois. 

A drawback of the strategy shown above is that oligomer growth is relatively inefficient. It is this reason that makes stepwise addition strategies most suitable for smaller oligomers. Another problem arises from the difficulties associated with separation of defective products, for example, octamer from nonamer. 

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Moore IS, Hill DJ, Mio MJ. Solid-phase synthesis of sequence-specific phenylacetylene oligomers. In Burgess K, editor. Solid-Phase Organic Synthesis. New York John Wiley Sons, Inc. 2000. p 119-147. 

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