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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