A Practical and Efficient Approach to PNA Monomers Compatible with Fmoc-Mediated Solid-Phase Synthesis Protocols
✍ Scribed by Andrea Porcheddu; Giampaolo Giacomelli; Ivana Piredda; Mariolino Carta; Giammario Nieddu
- Book ID
- 102176067
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 300 KB
- Volume
- 2008
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
A straightforward synthesis of orthogonally protected PNA monomers is described. Protected aminoethylglycine (Aeg) monomers were efficiently prepared by reductive amination of N‐Fmoc‐glycinaldehyde with glycine methyl ester and the subsequent acylation of the free amine with N‐bis‐Boc‐protected nucleobase acetic acids. The exocyclic amine group of the nucleobases, including the notoriously difficult‐to‐protect guanine nucleobase, was protected with a bis‐Boc carbamate group; this increased the solubility of the nucleobases in the most common organic solvents. The current protocol allows all Aeg monomers to be prepared on both the micro‐ and macroscale, which avoids or minimizes the use of toxic reagents or solvents, and moreover, cheap starting materials are used. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)