Beilstein J. Org. Chem.2018,14, 253–281, doi:10.3762/bjoc.14.17
oligonucleotidemimics that consist of a peptide-like backbone. Although the idea of replacing the whole sugar-phosphate backbone of DNA with a completely unrelated scaffold such as peptide had been around since the 1970s [20], it was not until the 1990s that the first PNA system with an N-2-aminoethylglycine
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Graphical Abstract
Figure 1:
The design of classical DNA molecular beacons.
Beilstein J. Org. Chem.2014,10, 1151–1158, doi:10.3762/bjoc.10.115
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Keywords: labile linker; morpholino oligomers; oligonucleotidemimics; solid-phase-supported peptide synthesis (SPPS); Introduction
The phosphorodiamidate morpholino oligomers (PMO) and peptide conjugated PMO (PPMO) are currently promising candidates for antisense therapy of a number of infectious and
positively charged centers in oligonucleotide analogues results in increased water solubility and higher thermal stability of complementary duplexes of such oligonucleotidemimics with nucleic acids [14][15]. Some conformationally restricted protonated PNA or pyrrolidine oligonucleotidemimics exhibit
, methylenecarboxamide (glycine) oligomers (MorGly) (Figure 1A), being protonated at physiological pH, seem to be promising candidates for the development of novel antisense oligonucleotidemimics.
A convenient synthetic procedure was previously described for protected monomers 1a–d (Figure 1B) necessary for the
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Graphical Abstract
Figure 1:
Morpholinoglycine oligomers (A) and protected monomers 1a–e (B) for their synthesis.