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BOC Sciences offers PNA monomer synthesis service that can be customized to meet the specific needs of our clients, including the choice of nucleobases, protecting groups, and linkers. With our expertise in synthetic chemistry and nucleic acid analogs, we are committed to providing high-quality PNA monomers to support the development of innovative applications in the field of nucleic acid research.
Peptide nucleic acids (PNAs) are nucleic acid analogs that have attracted much attention due to their unique properties, such as high binding affinity and specificity to complementary DNA and RNA strands, and resistance to nuclease degradation. PNA monomers are the building blocks used for the synthesis of PNA oligomers. They consist of a pseudopeptide backbone composed of N-(2-aminoethyl)glycine units and nucleobase moieties, such as adenine, cytosine, guanine, thymine, or uracil, attached to the backbone through a methylene carbonyl linker. The backbone is achiral and neutral, which allows for high binding affinity and specificity to complementary DNA and RNA strands.
At BOC Sciences, we offer a comprehensive PNA monomer synthesis service:
The amino and nucleobase functionalities are protected using appropriate protecting groups to prevent unwanted reactions during the synthesis. For example, the amino of the N-(2-aminoethyl)glycine unit can be protected using the tert-butyloxycarbonyl (Boc) or the 9-fluorenylmethyloxycarbonyl (Fmoc) group. The nucleobase can be protected using the dimethoxytrityl (DMT) or the benzoyl (Bz) group.
In the synthesis of PNA monomers, the carboxylic acid is typically activated using a coupling reagent, such as N,N'-diisopropylcarbodiimide (DIC) or N,N'-dicyclohexylcarbodiimide (DCC), in the presence of a catalyst (DMAP or N-methylimidazole).
The coupling of the nucleobase to the activated carboxylic acid is typically achieved using standard peptide coupling reactions, such as amidation or esterification. The reaction conditions depend on the specific nucleobase and protecting group used in the synthesis. For example, coupling reaction can carried out in dimethylformamide (DMF) solution under alkaline conditions with the addition of triethylamine (TEA).
The deprotection strategy depends on the specific protecting groups used in the synthesis. For example, the commonly used Fmoc protecting group on the amino group can be removed using a solution of piperidine in DMF. The DMT or Bz protecting groups on the nucleobase can be removed using an acid such as TCA (trichloroacetic acid) or TFA (trifluoroacetic acid), respectively.
PNA monomers can be used for the synthesis of PNA oligomers, which have a wide range of applications, including:
