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A Practical and Efficient Approach to PNA Monomers Compatible with Fmoc‐Mediated Solid‐Phase Synthesis Protocols
Author(s) -
Porcheddu Andrea,
Giacomelli Giampaolo,
Piredda Ivana,
Carta Mariolino,
Nieddu Giammario
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800891
Subject(s) - chemistry , nucleobase , monomer , protecting group , reductive amination , amine gas treating , combinatorial chemistry , acylation , organic chemistry , polymer , dna , catalysis , biochemistry , alkyl
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)