3-(2,5-Cyclohexadienyl)-L-alanine (1,4-Dihydro-L-phenylalanine)
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Its Synthesis and Behaviour in the Phenylalanine Ammonia-Lyase Reaction

Table 1:

Experimental results of the Birch reduction of L-phenylalanine with different proton sources.

 
No
metal
proton source
yield
2,5-dihydro isomer a)
1,4-dihydro isomer a)
L-phenylalanine a)
1
Li
tert.-butanol
92.7 %
96.9 %
1.5 %
1.3 %
2
Li
ethanol
87.7 %
88.8 %
3.0 %
7.8 %
3
Li
CH3COONa
1.0 %
100.0 %
n.d.
n.d.

a) calculated from 1H-NMR.
n.d. = not detectable

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