Synthesis of 15N-labelled chiral Boc-amino acids from triflates: enantiomers of leucine and phenylalanine
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 11-14
- https://doi.org/10.1039/p19930000011
Abstract
An efficient synthesis of 15N-labelled chiral Boc-amino acids by triflate alkylation of di-tert-butyl [15N]imidodicarbonate is reported. Both enantiomers of Boc-leucine and -phenylalanine were synthesized from commercial α-amino acids of opposite configuration viaα-hydroxy carboxylic acids provided by diazotization, thus extending the scope of an earlier exploratory study. The high chiral purity of the final products was confirmed by HPLC. These labelled amino acid derivatives are suitable for direct application to the synthesis of labelled peptides.Keywords
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