1. Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization
- Author
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Leif Christensen, Kim L. Dueholm, Ole Buchardt, Michael Egholm, Carsten Behrens, Henrik Hansen, Kenneth H. Petersen, Peter E. Nielsen, Tore Vulpius, and Rolf H. Berg
- Subjects
chemistry.chemical_compound ,chemistry ,Peptide nucleic acid ,Guanine ,Stereochemistry ,Organic Chemistry ,Peptide synthesis ,Nucleic acid ,Oligomer ,Cytosine ,Thymine ,Nucleobase - Abstract
The preparation of mixed-sequence PNAs (PNAs containing the four natural nucleobases; thymine, cytosine, adenine, and guanine) is described. The PNA monomers containing thymine, Cbz-protected cytosine, or adenine or benzyl-protected guanine were prepared via convergent syntheses. Subsequent to introduction of the carboxymethyl linker at N-1 of the pyrimidines or N-9 of the purines and suitable protection of exocyclic groups, the nucleobase derivatives were coupled to the Boc-protected backbone esters 10a or 10b and finally hydrolyzed affording the monomers 12a-d. The exocyclic amino groups of cytosine and adenine were protected with a benzyloxycarbonyl group. The exocyclic amino groups of guanine was left unprotected whereas O 6 was protected as the benzyl ether. Two mixed-sequence 10-mers, each with five purines incorporated, and a mixed-sequence 15-mer containing seven purines were assembled essentially following standard solid phase peptide synthesis protocols
- Published
- 1994
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