Synthesis and coupling reactions of alpha,alpha-dialkylated amino acids with nucleobase side chains.

Azumaya, I; Aebi, R; Kubik, S; Rebek, J · Proc Natl Acad Sci U S A · 1995

basic_science · Level V

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Abstract

Several di- and tripeptides containing protected purine (adenine) and pyrimidine (thymine) residues on their side chains were synthesized. The parent amino acids alpha, alpha-dialkylated in a symmetrical manner. An effective coupling procedure was developed for these sterically hindered amino acids: the fluoren-9-ylmethyloxycarbonyl-protected amino acid was dehydrated to its oxazolinone form, which was coupled in good yields with amino esters in hot tetrachloroethane.

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