Amino acids bearing nucleobases for the synthesis of novel peptide nucleic acids

Abstract

All of the four nucleobases found in DNA have been incorporated in their protected form into the 4-position of N-tert-butoxycarbonyl-L-proline methyl ester with cis-stereochemistry. An efficient route for the synthesis of N-tert-butoxycarbonyl-trans-4-hydroxy-D -proline methyl ester has been developed from which the enantiomers may be synthesized. In addition an efficient synthesis of N-tert-butoxycarbonyl-N-(2-hydroxyethyl)glyc ine methyl ester has been achieved and its hydroxy group replaced with protected nucleobases using the Mitsunobu reaction

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