Journal of the Chemical Society. Perkin transactions I p. 3545 - 3548 (1994)
Update date:2022-08-04
Topics:
Easton, Christopher J.
Hutton, Craig, A.
The four stereoisomers of <3-2H1>phenylalanine have been prepared, each as a single enantiomer in ca. 98percent diastereoisomeric excess and with ca. 99percent deuterium incorporation, by side-chain bromination of phenylalanine derivatives, followed by deuteriolysis of each of the diastereoisomeric product bromides with deuterium over 5percent palladium-on-carbon.The latter reactions proceeded with retention of configuration. (2R,3S)-<3-2H1>Phenylalanine reacted with (S)-phenylalanine ammonia-lyase to give <3-2H1>-trans-cinnamic acid, with 92percent deuterium incorporation, while the (2R,3R)-stereoisomer of the deuterated phenylalanine gave <3-2H1>-trans-cinnamic acid with 27percent deuterium incorporation.These results indicate that reaction of (R)-phenylalanine with the enzyme involves mainly loss of the 3-pro-R hydrogen and ammonia, in an antiperiplanar elimination process analogous to that previously reported for (S)-phenylalanine, while a minor pathway for reaction of (R)-phenylalanine is either isomerization to (S)-phenylalanine, before elimination, or synperiplanar elimination.
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