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

Porcheddu, Andrea and Giacomelli, Giampaolo and Piredda, Ivana and Carta, Mariolino 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, Vol. 2008 (34), p. 5786-5797. eISSN 1099-0690. Article.

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DOI: 10.1002/ejoc.200800891

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
ID Code:1729
Status:Published
Refereed:Yes
Uncontrolled Keywords:Peptide nucleic acids, guanine, protecting groups, solid-phase synthesis
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Wiley
eISSN:1099-0690
Additional Information:Pubblicato online il 29 ottobre 2008.
Deposited On:18 Aug 2009 10:05

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