117370-55-5Relevant academic research and scientific papers
Preparation of (R)-2-azidoesters from 2-((p-nitrobenzene)sulfonyl)oxy esters and their use as protected amino acid equivalents for the synthesis of di- and tripeptides containing D-amino acid constituents
Hoffman,Kim
, p. 3007 - 3020 (2007/10/02)
(R)-2-Azidoesters and their derived (R)-2-azido acids are readily prepared from common amino acids by an inversion methodology that employs (S)-2-nosyloxyesters as key intermediates. The (R)-2-azidoesters can be used as protected amino acid equivalents in peptide synthesis. Basic hydrolysis frees the carboxyl group. Triphenylphosphine/water is used to free the amine group. By these reactions a variety of L-D and D-L dipeptides, L-D-L tripeptides, and depsipeptides can be prepared easily in good yields, and without detectable epimerization.
