C5-pyrimidine-functionalized morpholino oligonucleotides exhibit differential binding affinity, target specificity and lipophilicity

Abstract

C5-substituted uridine and cytidine morpholino chlorophosphoramidate monomers were synthesized and incorporated into a 12-mer Phosphorodiamidate Morpholino Oligonucleotide (PMO) using semi-automated solid phase synthesis. 5-Substituted pyrimidines incorporated PMO significantly increase the...

Morpholine Scaffolds’ Preparation for Foldamers’ Design and Construction

“…Similarly, arylation of iodouridine 17 with aryl boronic acids were successfully realized. [30] A similar approach was disclosed by Abramova. In this case, the process involves the iodination of the nucleoside before construction of the morpholine moiety (Scheme 10, path b).…”

“…alkynyl‐substituted compounds 18 were synthesized in good yields through Sonogashira coupling reactions. Similarly, arylation of iodouridine 17 with aryl boronic acids were successfully realized [30] . A similar approach was disclosed by Abramova.…”

Synthesis and Biophysical Studies of High-Affinity Morpholino Oligomers Containing G-Clamp Analogs

“…The chlorophosphoramidate monomers were used in the synthesis of two 12-mer PMOs (5′-TTTTACT C ACAT-3′ and 5′-TGT C ATC C CATT-3′, the bold letters are the sites of a single modification) on Ramage Chemmatrix resin following the reported procedure (Figure S2). , The PMOs were purified by HPLC and characterized by MALDI-TOF (Table S1 and Figures S3–S15). A postsynthetic strategy was adopted for the conversion of amine to guanidinium group as previously reported .…”

“…Tetrabutylammonium fluoride (TBAF)-mediated deprotection of the TBDPS group yielded 1k (Scheme ). The chlororophosphoramidate monomer 1l was synthesized using the LiBr-TMG method reported previously . Phenoxazine derivatives ( 2b – d ) were synthesized using a similar strategy (Scheme ).…”

“…The chlororophosphoramidate monomer 1l was synthesized using the LiBr-TMG method reported previously. 24 Phenoxazine derivatives (2b−d) were synthesized using a similar strategy (Scheme 5).…”