A practical and efficient approach to PNA monomers compatible with Fmoc-mediated solid-phase synthesis protocols

Porcheddu, Andrea, Giacomelli, Giampaolo, Piredda, Ivana, Carta, Mariolino ORCID: https://orcid.org/0000-0003-0718-6971 and Nieddu, Giammario 2008. A practical and efficient approach to PNA monomers compatible with Fmoc-mediated solid-phase synthesis protocols. European Journal of Organic Chemistry 2008 (34) , pp. 5786-5797. 10.1002/ejoc.200800891

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	Peptide nucleic acids; Guanine; Protecting groups; Solid-phase synthesis
Publisher:	Wiley
ISSN:	1434-193X
Last Modified:	24 Oct 2022 11:49
URI:	https://orca.cardiff.ac.uk/id/eprint/49462

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