2002/11/01 by Arndt M. Brückner, Arndt M. Brückner, Harald W. Schmitt +2
Chemistry · Biochemistry, Genetics and Molecular Biology · Medicine · #Ferrocene Chemistry and Applications #DNA and Nucleic Acid Chemistry #Pneumocystis jirovecii pneumonia detection and treatment
paper · pdf · doi:10.1002/1522-2675(200211)85:11<3855::aid-hlca3855>3.0.co;2-a
The synthesis of thyminyl-, uracilyl-, cytosinyl-, and guaninyl-β3-amino acids and the oligomerization of the cytosinyl- and guaninyl-β3-amino acids to β-homoalanyl-PNA are presented. The pyrimidinyl nucleobases were connected to the γ-position of β-homoalanine by Mitsunobu reaction with a β-homoserine derivative or by nucleophilic substitution of methanesulfonates. For the preparation of the guaninyl-β3-amino acid, a β-lactam route was established that might be of interest also for the synthesis of other β3-amino acid derivatives. The cytosinyl and guaninyl building blocks were oligomerized to hexamers. They form quite stable self-pairing complexes in H2O as indicated by temperature dependent UV and CD spectroscopy.