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Synthesis of Phosphonoglycine Backbone Units for the Development of Phosphono Peptide Nucleic Acids
Author(s) -
Doboszewski Bogdan,
Groaz Elisabetta,
Herdewijn Piet
Publication year - 2013
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.201300523
Subject(s) - chemistry , phosphodiester bond , phosphonate , nucleobase , nucleic acid , combinatorial chemistry , stereochemistry , glycine , peptide nucleic acid , peptide , amino acid , dna , organic chemistry , biochemistry , rna , gene
A series of phosphono‐modified backbone mimics based on achiral and chiral N ‐(dihydroxypropyl)glycine units were obtained by sequential addition of phosphonate and nucleobase moieties to suitably protected dihydroxypropylamines. Simple synthetic strategies enabled the preparation of various target derivatives that will be useful as building blocks for the preparation of new synthetic polymers containing a phosphonate internucleotide linkage in place of the standard phosphodiester bond.