A Fmoc-based submonomeric strategy for the solid phase synthesis of optically pure chiral PNAs |
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Authors: | Tullia Tedeschi Francesca Maffei Roberto Corradini Rosangela Marchelli |
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Institution: | Dipartimento di Chimica Organica e Industriale, Università di Parma, Viale G.P. Usberti, 17a, Parma 43100, Italy |
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Abstract: | A new submonomeric approach for the Fmoc solid phase synthesis of chiral PNAs is reported here. The design and synthesis of a new d-lysine-based Fmoc submonomer obtained by replacing the nucleobase residue with an Alloc group, compatible with Fmoc chemistry, is described starting from d-lysine and Fmoc-aminoacetaldehyde. The desired submonomer was obtained in high yield with no racemization. The conditions for synthesizing a chiral PNA dimer on solid support by a submonomeric approach have been optimized, allowing to obtain the desired PNA with a very high optical purity. |
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Keywords: | Chiral PNAs Submonomeric strategy Optical purity Fmoc strategy |
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