Bioorganic and Medicinal Chemistry Letters
Bioorganic and Medicinal Chemistry Letters
5 years ago

PNA monomers fully compatible with standard Fmoc-based solid-phase synthesis of pseudocomplementary PNA

PNA monomers fully compatible with standard Fmoc-based solid-phase synthesis of pseudocomplementary PNA
Here we report the synthesis of new PNA monomers for pseudocomplementary PNA (pcPNA) that are fully compatible with standard Fmoc chemistry. The thiocarbonyl group of the 2-thiouracil (sU) monomer was protected with the 4-methoxy-2-methybenzyl group (MMPM), while the exocyclic amino groups of diaminopurine (D) were protected with Boc groups. The newly synthesized monomers were incorporated into a 10-mer PNA oligomer using standard Fmoc chemistry for solid-phase synthesis. Oligomerization proceeded smoothly and the HPLC and MALDI-TOF MS analyses indicated that there was no remaining MMPM on the sU nucleobase. The new PNA monomers reported here would facilitate a wide range of applications, such as antigene PNAs and DNA nanotechnologies.

Publisher URL: www.sciencedirect.com/science

DOI: S0960894X17306170

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