Stereoselective β-labelling of aromatic amino-acids with deuterium and tritium
- 1 January 1973
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- Vol. 2, 115-120
- https://doi.org/10.1039/p19730000115
Abstract
Tyrosine and phenylalanine, labelled stereoselectively with deuterium and tritium in the β-methylene groups, have been prepared via cis-hydrogenation of appropriate, β-labelled α-acylaminocinnamic acids obtained from the corresponding benzylideneoxazolinones. The configuration of (βR)-L-[β-2H]tyrosine was confirmed by ozonolysis of its racemate to give the racemate of (βS)-L-[β-2H]aspartic acid of known stereochemistry. The incorporation of the (βR)-[β-3H]- and (βS)-[β-3H]-forms of tyrosine into haemanthamine in ‘Texas’ daffodils was studied to show that hydroxylation of the original methylene group occurred highly stereospecifically with retention of configuration.Keywords
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